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Matthew Stern
Growth Expert for Entrepreneurs | Building High-Performing Businesses & Leaders
Matthew Stern is a seasoned entrepreneur with over 18 years of experience, dedicated to helping businesses break through growth ceilings. He understands the challenges of stagnant sales, limited reach, and unfulfilled potential that can hinder entrepreneurial success. Matthew aims to assist entrepreneurs in developing a healthy work-life balance, continuously learning and growing in their ventures, building loyal customer bases, and achieving explosive business growth.
Leveraging his extensive experience, Matthew provides actionable strategies to help businesses overcome overwhelm, optimize marketing campaigns, develop strong leadership skills, and attain work-life balance. He focuses on instilling a growth mindset in entrepreneurs and their teams to foster innovation and resilience.
With a clear vision and roadmap, Matthew envisions entrepreneurs achieving ambitious business goals, leading high-performing teams, making confident decisions, feeling energized, and spending quality time with their families. He warns against settling for stagnation and emphasizes the risks of staying stuck in mediocrity and refusing support from experts. Matthew invites entrepreneurs to unlock their growth potential through personalized guidance and proven strategies.
Matthew Stern holds a Bachelor's degree from the University of California, Berkeley. He has held key positions in various organizations, including Co-Founder at Cheatcode Foundation, Chief Executive Officer at The Stern Group, Chief Product Officer at Digital Media Solutions Group, Founder at TapRush, Co-Founder at BlitzSF, Partner at Angelrush Ventures, and Media Director at Syndero.
Highlights
At the Top of the Slide: Lessons in Bravery from the Playground
Last night, an ordinary evening at the playground with my daughter transformed into a profound life lesson. My daughter, now 3.5 years old, has always been adventurous at our local park. From 8 months old, she'd tackle all the slides, including the daunting, windy one. But recently, she's grown inexplicably fearful of this slide she once conquered without a second thought.
After climbing to the top last night, she froze, overwhelmed by fear. For nearly twenty minutes, my wife and I reassured her, promising to catch her and reminding her of her past bravery. Time and again, she'd approach the edge, only to retreat in panic. Then, in a moment of maternal brilliance, my wife asked, “Do you need a push?” and offered to climb up and give her the gentle nudge she needed. I was certain this would end in a meltdown—but I was wrong. The moment she descended and rounded that first turn, her face lit up with the brightest smile, and she exclaimed triumphantly at the bottom:
"I DID IT, I AM SO BRAVE, I WANT TO GO AGAIN!"
She repeated her new victory lap over and over, her joy and pride filling the playground. We celebrated her newfound courage well into the night.
After the nighttime routine, my wife noticed I seemed off. I'd been filled with anxiety about a new venture I'm about to launch—I’ve been doing this for 15 years yet always had partners alongside me to share in the planning, strategy, and risk. I confessed my fears, admitting I felt just like our daughter at the top of the slide, paralyzed by what was once familiar territory.
With her unwavering support and a smile, my wife said, “Do you need a push?” and reminded me that I wasn't alone. I have a dedicated team, a wealth of experience, and a history of successfully navigating these waters. Her words mirrored the encouragement we'd given our daughter: “It’s the same slide you’ve been on your whole life. Do you need a little push?”
This morning, with a fresh perspective, I'm ready to embrace the slide. Though the fear of the unknown lurks, the excitement of potential success is compelling. Just like my daughter learned, I'm reminded that sometimes, the only way to overcome our fears is to go down that slide—because the joy of overcoming our doubts is always worth the initial fear.
As entrepreneurs, we're frequently perched at the top of various slides. We spend our lives climbing up and wondering if we should take the plunge. Let's remember that we often find our true joy and growth not in safe contemplation at the top, but in the exhilarating ride down.
To everyone standing at the top of their slides, remember, the journey down can be thrilling. And just like my daughter discovered, once you start sliding, you might just find it's exactly where you're meant to be.
Going All In vs. Side Hustles: Navigating the Entrepreneurial Journey
Navigating the entrepreneurial landscape involves balancing risk, ambition, and personal commitments. Having juggled multiple ventures while managing family responsibilities, I've learned the reality of trying to "do it all."
Initially, managing various ventures alongside personal commitments seemed thrilling, suggesting limitless potential. However, this approach led to spread resources too thin, limiting each venture's potential.
Time and energy are finite. Balancing work and home demands more than could be given without sacrificing output quality or personal well-being. Acknowledging these limits, I refocused, leading to accelerated progress in my relationships, health, and business.
The path to the success I desired lay in committing fully to one project. This means channeling all your passion and resources into a venture with the highest growth potential.
The decision to focus involves managing fear, notably the fear of risking my family’s security—a mistake my father made that I am keen to avoid. With a solid financial foundation and a strategic plan that includes realistic milestones, I am prepared to take calculated risks that won’t jeopardize my family’s well-being. Choosing between multiple side hustles and going all in on one main venture is profound. It requires understanding personal limits, aligning professional aspirations with familial duties, and managing one's ego alongside unwavering self-belief.
In entrepreneurship, as in life, the biggest risk can often be not taking one at all. When the groundwork is laid, taking that calculated leap to go all in might just be the key to building something truly meaningful.
