Life, pressure and purpose with Gregg Alvarez
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In our latest podcast episode of Uncharted Your Sidekick for Life Podcast, we talk with Gregg Alvarez, who shares his journey shaped by his experiences in Austin, Texas, his military service, and his ventures into the world of technology and investment.
Growing up in Austin, Gregg attended Westlake High School, known for its academic reputation, but his experience during those years was not defined by success.
Instead, Gregg describes high school as a difficult period, where he faced personal challenges and lacked a clear vision for the future.
“High school was a tough time in my life. I wasn’t sure what I wanted to do and struggled with personal challenges. It was more about getting through than excelling.”
Following high school, Gregg’s life took a transformative turn when he joined the military. This decision broaden his perspective and instilled in him a strong sense of discipline and perseverance. Serving alongside people from various walks of life, Gregg learned invaluable lessons about collaboration and adaptability.
“The military was an amazing experience. I learned how to work with people from all walks of life. It opened my eyes to how much bigger the world is and how many different ways there are to live and think.”
After his time in the military, Gregg didn’t return to his previous job.
Instead, he found himself drawn to a new and evolving world: technology.
One of his earliest roles was with Citysearch, an online city guide that sought to introduce local businesses to the internet. During a time when the concept of the internet was still foreign to most people, Gregg was knocking on doors, explaining why businesses needed an online presence.
“My first job was literally selling the internet.”
“I would knock on doors and explain to business owners what the internet was and why they needed to be on it. No one had heard of it—it was exciting and challenging.”
This initial exposure to the internet’s potential set the stage for Gregg’s future endeavors. He later worked on groundbreaking projects like Cars.com and helped introduce other innovative platforms to the market.
His ability to see opportunities where others saw uncertainty fueled his entrepreneurial spirit. Gregg’s success in the tech world led him to a career in entrepreneurship and angel investing. Over the years, he has worked closely with a variety of early-stage companies, offering financial support and strategic advice.
For Gregg, angel investing is about more than just capital; it’s about believing in ideas and helping them grow.
“Angel investing is about more than just money, It’s about believing in a vision before anyone else does and helping turn that idea into something real.”
As his career progressed, Gregg’s approach to risk evolved. While he was once drawn to the excitement of high-risk startups, he now seeks out more stable ventures that still offer room for innovation. His investment in Proforma, a marketing services franchise, reflects this shift.
“I’ve become more risk-averse with age, but I’m still passionate about innovation. The key is aligning business goals with innovative ways to achieve them.”
Throughout his journey, mentorship has played a pivotal role in Gregg’s success.
From military officers to business leaders, Gregg has always sought guidance from those more experienced.
Now, he’s committed to providing the same mentorship to younger entrepreneurs.
“Mentorship has been critical in my life. Whether it was a priest, my military officers, or business leaders, I always sought out people who could help me grow. And now, I’m happy to do the same for others.”
In the podcast episode, the discussion shifts to the challenges facing Gen Z today, particularly around social media and societal pressures. Bella, a Gen Z participant, shares her frustration with how social media has changed relationships, making it harder to form meaningful connections.
“I was on social media in middle school, but it wasn’t like it is now. I can’t imagine being a little 12-year-old girl and having to figure everything out with social media in the way.”
Gregg sympathizes with Bella’s concerns. He explains how social media can create the illusion of connection while lacking the depth of real-world relationships.
“Social media makes us think we’re building community, but it’s not. We’re spending time and energy on something that isn’t reciprocal. Real relationships are built on give and take, and social media doesn’t offer that.”
“It’s like junk food versus wholesome food; social media is the junk food of relationships.”
Another participant, Landon, discusses the immense pressure to succeed academically and plan for the future, particularly during his high school years.
“High school was hard enough, but by the time I hit junior and senior year, it felt like all anyone cared about was, ‘What’s next? What are you doing for college?’ It was overwhelming.”
Gregg relates to this experience, noting how his own children are already feeling similar pressures.
“I see the same thing with my 12-year-old twins. They’re already feeling the pressure of school and future decisions. It’s important for them to know that they’re enough just as they are, right now.”
Pressures have changed across generations. For Baby Boomers, success was often tied to traditional values like job stability and homeownership. Millennials, on the other hand, face financial pressures from student debt and the need to balance their careers with the demands of the digital age. Gen Z, the first fully digital generation, faces unique stressors from social media, cyberbullying, and the climate crisis.
One of our hosts, Leon points out that
“Gen Z is growing up in a world that’s changing so fast. They’re being asked to plan for futures that don’t even exist yet. We need to give them space to explore without feeling like every decision they make is life or death.”
The importance of building real-world communities also emerges as a key theme in the episode. In a world dominated by digital interactions, Gregg stresses that true relationships are built through face-to-face interactions and meaningful exchanges.
“Social media gives us the false sense that we’re connected to hundreds of people, but those relationships are often hollow.”
For Gregg, the key to success isn’t just about career achievements but about building real relationships and contributing to the communities around you.
“When you find ways to be valuable in your community, people recognize that. That’s how deeper relationships form. That’s how I’ve found mentors throughout my life—by showing up, being helpful, and being willing to contribute.”
Listen to Uncharted Your Sidekick for Life: Episode 5, Season 2 with Gregg Alvarez
Greg Alvarez: Gregg Alvarez has over 12 years of experience in advising, consulting, and angel investing, primarily helping early-stage companies scale. He recently invested in a Proforma franchise, leveraging his background in sales and marketing to support businesses with print, promotional items, and loyalty programs. Gregg has worked extensively as an angel investor, focusing on startups with innovative ideas and often taking on active leadership roles.
Natalie Peyton: Peyton studied theatre and film in Australia, New York and LA and performed stand-up on the “three coasts.” She honed her podcast executive skills over the last 4 years developing and producing dozens of podcasts and even hosts a children’s mindfulness bedtime program
Leon Vanstone: Leon brings his curiosity and sharp interviewing skills to the table, facilitating insightful discussions with our mentors, extracting valuable lessons and insights to empower listeners on their own path to growth and achievement.
Dan Dillard: Dan, with his thoughtful approach and engaging style, delves into the minds of our mentors on the podcast, crafting compelling interviews that uncover the wisdom and experiences driving their success and impact.
This blog was written by Anais Schmidt, one of the hosts of the Uncharted Podcast. Anais is also an aspiring musician. When not in her studio, she tours Europe with Monte Mai.
If you would like to join the conversation email us at anais@foundingup.com
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