We recently had the chance to connect with Damon D’Amore and have shared our conversation below.
Hi Damon, thank you so much for joining us today. We’re thrilled to learn more about your journey, values and what you are currently working on. Let’s start with an ice breaker: When was the last time you felt true joy?
The morning I picked up my new puppy. I flew to Austin to pick him up and we drove back home on a two-day road trip.
Can you briefly introduce yourself and share what makes you or your brand unique?
I am a performance, communications and strategy advisor working one-on-one with C-Suite executives ranging from lrage legacy global corporations to high-growth venture and private-equity comapies for the better part of three decades.
Specifically, in the areas in which I have been working the past three decades from Fortune 500 C-Suite to exponential growth founders:
* Psychological Performance and Emotional Relief
* Storytelling and Stakeholder Engagement
* Navigating Ambiguity and Crisis Leadership
* Women Who Lead (more than half of my clients are women in the C-Suite)
I believe that teaching, mentoring and sharing the journeys of knowledge exploration are foundational to performing at a high-level in any profession. Over the years I have been fortunate to have had many venues and communication channels open for me to do exactly that. Public and corporate speaking at events, conferences and board meetings worldwide, teaching and mentoring at Top 25 business school MBA programs here in the US, even hosting an online show on business and entrepreneurship for Discovery Channel and American Express.
While the nature of my work with clients is one-on-one, confidential and personalized to each individual and scenario, there are fundamental lessons to be learned from each which I have enjoyed sharing with other leaders and aspiring leaders alike.
Appreciate your sharing that. Let’s talk about your life, growing up and some of topics and learnings around that. Who saw you clearly before you could see yourself?
My first true career mentor, his first name is Bill. I had already enjoyed successful careers on Wall Street and in Hollywood and for the first time was venturing out into the world of being an entrepreneur and a true founder.
I held a number of false beliefs about my limitations as a first time founder, especially being almost 40 years old compared to all of the ‘young entrepreneurs’ highlighted in media. Bill was a career entrepreneur – many successes and also many failures and he saw deep inside of me the potential and raw foundation to thrive in entrepreneurship. Over the next year of our relaionship he mentored me into raising my first rounds of capital from investors to launch a company and, eventually, over time became my business partner and peer in a later venture.
Along the way from Wall Street starting at 21 years old through Hollywood in my 30s there were always potential mentors who thought I had potential to do bigger things but none put their time and resources behind those beliefs in me as did Bill and I am eternally grateful.
Today I mentor as many founders and also students as I can each year to pay forward the gratitude.
What did suffering teach you that success never could?
That you must love the journey that you decide to take because it is in the journey, process and years of striving towards success – one step forward two steps back again and again – that you must learn to be resilient and realize how lucky you are to be suffering in service of something you love.
One of my favorite mantras is from Nietzsche: “One must imagine Sisyphus happy.”
Success is wonderful when you finally attain it but it is a moment, a few moments at best and it’s fleeting.
One of the worst feelings in the world I never expected to experience was just a few days after a massive success in business I had been working towards and sacraficing for years to accomplish. I felt empty as if now I had no goals because I hadn’t planned what would be next in my life – the next big challenge. I felt like a shark in a fish tank, like I was built to swim and hunt and be in constant motion – the journey had taken years and I had grown to love the struggle – then waking up without a giant goal to focus on and start moving towards daily I was lost.
I think our readers would appreciate hearing more about your values and what you think matters in life and career, etc. So our next question is along those lines. What would your closest friends say really matters to you?
That I go out of my way to help others – especially those less fortunate and that I am one of the most resilient people they have ever known.
Each year around the holidays when I do my annual review of work and life and plan the next year I email 5 professional and 5 personal pals and ask them if they woke up tomorrow and heard that I had passed away, what is the first thing that comes to mind – a sentence or even a word. For the past five years I’ve averaged 90% think of my passion for helping others and 80% their first word association is reslience, or grit.
That makes me happy because I am living my values and don’t need to shout them or wear them on a shirt – my actions are instilling those values in others as the core associations with who I am.
Thank you so much for all of your openness so far. Maybe we can close with a future oriented question. When do you feel most at peace?
I feel most at peace when I am on a trip or vacation, having left the office in great shape with happy clients and measurable ROI for everyone I am engaged with. That allows me to relax at my core. I am happiest then usually in a quiet wilderness area with my pup and partner if I am dating at the time. Chill time and training time with my high-drive working line dog are my Zen times and what I look forward to.
Contact Info:
- Website: https://legacymentor.co/
- Linkedin: https://www.linkedin.com/in/damondamore/
- Other: https://damondamore.substack.com/





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