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Check Out Chris Fiacco’s Story

Today we’d like to introduce you to Chris Fiacco.

Hi Chris, please kick things off for us with an introduction to yourself and your story.
I am the President as well as one of the founders of Bourbon & Bowties Baltinore, Inc. Our marquis fundraising event is Bourbon & Bowties. In its original form, Bourbon & Bowties was a small patio party thrown by the owner of the Quintessential Gentlemen, Craig Martin and the Managing Partner of the Baltimore Capital Grille, Jim Kinney. 12 years ago, I approached the two of them and proposed expanding this ‘pass the hat’ style charity event into Bourbon & Bowties in its modern form. They agreed and we also opted to formally create a 501(c)3 charity. Since that time, 12 years ago, our event has now grown to one of the top annual fundraisers in the city of Baltimore. We currently host over 1,000 guests with tickets selling out in minutes. Each year the event gets a little more special and since the beginning, we’ve raised more than $1 million dollars for local, environmental and military charities.

A little of the backstory and why behind all of this is simple. The founders and each member of our board are Baltimore or Maryland based businessmen. We all have ties to the community as well as the Chesapeake Bay. Some of us have military backgrounds or affiliations with the military through relatives. Collectively, we wanted to throw a party style event, with a unique atmosphere and feel to it, that directed funds to deserving charities we are passionate about. Part of the charm and allure of Bourbon & Bowties is that it’s not a stuffy, sit-down event with lots of speeches. Instead, it’s an experience! It caters to men and women alike. While Bourbon may be in the name, there are a myriad of different types of libations beyond the namesake, incredible food from dozens of local restaurants and a Preakness like dress code that gets everyone excited for months in advance about planning their outfit. Each year, we try to add a new touch to the event to enhance the atmosphere and environment.

Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
Success rarely happens in a straight line. We’ve absolutely encountered some challenges along the way, but as we like to say in the military, “What does not kill you, only makes you stronger!” When we first attempted to move Bourbon & Bowties from the Capital Grille to its first real venue, The Baltimore Musuem of Industry, we had only 20 tickets sold and more than $10,000 spent for an event that was less than 2 weeks away. Fortunately, with a hard push in the last few days leading up to the event, we were able to get 120 people to attend. All were blown away by the experience and kept asking where the rest of the people were. Our response, “Next year, tell a friend.” And sure enough, they did. We doubled in size the next year and a couple years later got too big for the BMI. That resulted in us rloacting to Rye Street Tavern and the Sagamore Distillery property. While that was a wonderful venue, it was not well suited to handle inclement weather. Just days before our second event at Rye Street, we were looking at an awful weather forecast. Miraculously, our Executive Director, Abby Hensley was able to pivot a 700-person event from Rye Street to the B&O Railroad Musuem in only 48 hours and we pulled off the best Bourbon & Bowties the city had yet to see that night.

Along the way, we lost a wonderful event planner when she returned to working full time for one of the charities we had been supporting back then. While it was a short-term blow that had us all concerned, it quickly led to us finding Abby Hensley, our present Executive Director. Abby is an absolute magician in the way she helps make this event come together every year. ‘Herding the cats,” of our board is no easy task and she does it wondefully! We also lost one of our Founders and Board Members along way. While it was a difficult and painful decision that threatened to break apart our team, in the end it led to us adding Chris Desautelle to our board. His addition has been exponentially beneficial. Chris is an incredibly successful businessman with a calm, highly thoughtful demeanor that continues to add value to our vision every day.

Like everyone in the city, we had to navigate COVID. This caused us to cancel one year’s event and the next year, pivot from our traditional May date that is always the Thursday in between the Kentucky Derby and Preakness, to executing in September. That meant the following year’s event only had a 6-month runway of planning and preparation to get back on track for the May date.

As you know, we’re big fans of you and your work. For our readers who might not be as familiar what can you tell them about what you do?
I started the first 8 years of my professional career as a United States Marine. I served as an infantry officer, a Reconnaissance Platoon Commander and then as a Company Officer at the United States Naval Academy. Upon leaving military service, I transitioned to the financial services industry. For 23 years, I worked for some of the leading asset management firms like BlackRock, New York Life Investments and Janus Henderson Investors. In this capacity I consulted with thousands of financial advisors on best practices for portfolio construction as well as practice management. I also spent close to a decade leading distribution professionals. In early 2023, two of my best clients, the founders of Shore to Summit Wealth Management, convinced me to leave the W2 employee world and become a business owner with them. Together, we bought a $300 million wealth management practice that I now run. I have since purchased a second wealth management practice and also am deeply involved with the rapid growth of Shore to Summit’s Wealth Management Partnership footprint across the country. What I am most proud of about this is the courage that it took to walk away from a very successful career in distribution and make a bet on myself. Fortunately, I had the tremendous support of my wife, and I had the backing and the mentorship of two great partners. Additionally, I have had the ability to leverage my experience as Marine Officer, a Distribution Professional and even as a founder of Bourbon & Bowties to help with the execution of this new endeavor. All of these are now contributing to the professional success that I am currently enjoying and the exciting future ahead.

What sets me apart from others….at a young age, I had a tremendous Marine officer mentor that taught me these 4 core tenants of leadership that I use as my guidepost in life, not just as a professional but also as a husband and parent:

Lead by Example
Take Care of Your People
Do What is Right
Have Fun

People feel your authenticity as well as your passion and conviction for the task at hand. If you execute with integrity and with real purpose the only thing left to achieve success is hard work. Hard work is something I have never shied away from.

What was your favorite childhood memory?
Seeing the ocean for the first time and then learning how to surf on it.

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