This isn’t your typical family business story.
Bobby started in finance, swore he’d never work with family, then life forced a pivot. Stepping in reluctantly, he helped scale the business to 40 locations and $50M, but success came at a cost: resentment, burnout, and the realization that growth without alignment is a trap.
So, he walked away.
Bobby went on to build Greenridge Wealth, a firm built on values, systems, and a team-first culture. His mission? Help founders build businesses that run without them so they can actually live.
In this episode, Bobby lays it all out. The toll of resentment. The dangers of tying your identity to your business. The hard decisions around rebuilding teams, shifting mindsets, and designing companies that can grow without you in the middle of everything.
This is about leadership, clarity, and doing it on your own terms. Not grinding forever. Not chasing empty success. Just building a business that serves your life, not the other way around.
So, if you’re building, scaling, or just trying to break free from the grind this episode is packed with insights you don’t want to miss. Grab your notepad, tune in, and start building a business that works for you, not the other way around.
In This Episode:
Building Greenridge Wealth Planning [00:02:20
Why Bobby Avoided the Family Business for So Long [00:03:40]
Health Scares Changed Everything [00:06:20]
Shifting From Scarcity to Abundance [00:09:40]
The Power of Peer-to-Peer Conversations [00:11:50]
Bobby’s Return to the Family Business With a New Vision [00:16:30]
The dangers of becoming emotionally tied to your business. [00:19:10]
The Importance of Making Yourself Obsolet [00:20:20]
Key focus on employee engagement and career growth within the business. [00:24:10]
Leveraging Strategic Partnerships for Growth [00:29:00]
The value of calculated risks, perseverance, and a willingness to change direction when necessary for business success. [00:32:50]
The Power of Relationships in Business. [00:37:00]
Designing a Business Around What You Actually Love [00:40:20]
How stepping back creates space for strategy and long-term vision. [00:43:00]
The Growth Junkie Trap [00:44:10]
Why Bobby believes in karma more than luck and how gratitude shifts your energy and outcome. [00:48:50]
Leadership Through Interaction & Decision [00:58:10]
Notable quotes:
"You've gotta tell me what it is. I wanna make the decisions. I have to be there not empowering other people to feel a sense of ownership. Just feeling like you're in the grind and you have to know everything." - Bobby [00:18:10]
"If that's really what fills your cup and gives you a sense of purpose, well then I have nobody, I'm not the person to tell you to do something that that is your purpose." - Bobby [0:19:40]
"It's not what you know. It's who you know." - Bobby [00:37:30]
“We overestimate what we can do in a year, but we underestimate what we can do in 10” Bobby at [00:56:10]
Resources and Links
Bobby Mascia:
LinkedIn
Instagram
Facebook
YouTube
Podcast
Website
Book
Insight Out:
Insight Out Show – Website
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