Learn from my Coach, From Losing $100K to Selling for $92M

Jan 15, 2025

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You know that moment when everything feels like it’s falling apart, and you’re not sure what to do next? That’s where Glen Hellman, the executive leadership coach and founder of CXO Elevate, shines. He’s taken companies from the brink of failure to massive success—including a $92 million exit—and now he helps entrepreneurs like us figure out how to keep going, grow smarter, and thrive.

Over the past year, Glenn’s been my go-to coach and has nudged (maybe beaten me up a few times, too) me to become more focused, more accountable, and ultimately more effective as I navigate the shifting paths of entrepreneurship.

In this episode, Glen shares how he went from fixing broken companies back in the dot-com era to helping founders avoid those pitfalls altogether. We talk about his no-nonsense coaching philosophy, how he helps entrepreneurs stay adaptable in constantly changing markets, and the long-term value of building resilience and accountability. If you’ve ever felt stuck or unsure about your next move, this episode is exactly what you need.

From Tech Sales to Transformational Coaching
Glen started his career selling high-end word processors long before companies like IBM or Xerox would give him a shot. His determination paid off, and he rose quickly through the ranks, eventually working at a software firm that went public. He later ventured into startups, gaining invaluable lessons from both successes and failures about managing risk and navigating markets.

Glen became known for turning around failing companies—cutting costs, reorganizing teams, and driving better results. But after years of what he calls “hospice care” for struggling businesses, he decided to shift gears. Instead of saving companies on the edge, he wanted to help entrepreneurs avoid those crises entirely, which led him to coaching.

Glen’s No-Nonsense Coaching Style
Working with Glen is anything but cookie-cutter. He’s not here to hand you a magic bullet or a perfect blueprint to follow. Instead, his approach is all about helping you figure out your path, stay accountable, and keep moving forward, even when the road gets bumpy. One of my favorite things Glen says is that running a business is like plotting a road trip to LA: you need to know where you’re going, but you’ve got to stay flexible for all the unexpected detours along the way.

What sets Glen apart is how he brings his lessons to life. He’s a storyteller. Every insight he shares is rooted in real-world experiences—both his own and those of the entrepreneurs he’s coached. He’s great at helping you break down what actually needs to get done to move forward. But he also pushes you to take a hard look at yourself. Are you on track? If not, what’s holding you back?

Glen understands that no two entrepreneurs are the same. Some of us need structure to stay on task, while others need a push to dream bigger or take risks. He tailors his approach to fit what you need—and trust me, he’ll make sure you follow through.

Finding the Right Coach
According to Glen, finding the right coach is like trying on gloves—you need a good fit. It’s about more than just credentials; it’s about trust, alignment, and personality. The best entrepreneurs he works with are the ones who stay curious, keep questioning their assumptions, and are open to growth.

That fit goes both ways. Glen is only interested in working with people he can genuinely help, and he creates a safe space where you can be totally honest about your challenges. That kind of radical transparency is where real growth happens.

Why Coaching Matters
For me, having Glen in my corner has been a game-changer. He’s helped me stay focused on what really matters, hold myself accountable, and keep pushing forward. Whether you’re working on finding product-market fit, pivoting your business, or scaling up, coaching isn’t just about solving problems—it’s about building habits and systems that help you stay on course.

Glen’s no-nonsense approach and focus on accountability have pushed me to step outside my comfort zone and grow in ways I didn’t expect. If you’re serious about leveling up, having the right coach can make all the difference. Glen’s helped me, and I know his approach can help you, too.

Key Insights:

Break plans into actionable steps. Forget long, rigid business plans. Instead, focus on what Glen calls a plan: “a verb, a noun, and a date.” Decide what needs to be done, by whom, and when—and stick to it.
Build accountability systems. Entrepreneurs often hold their teams accountable but lack someone to hold them accountable. Create regular check-ins with a coach or peer group to stay honest and focused.
Find product-market fit—continuously. Product-market fit isn’t a one-and-done task. Glen stresses the importance of regularly reevaluating your market to ensure your offering remains relevant, especially in shifting conditions.
Be radically transparent. Create a safe, nonjudgmental space for open discussions—whether with a coach, partner, or peer group. Transparency helps you make better decisions and address issues before they become crises.
Keep your vision front and center. Even in the chaos of day-to-day operations, ensure every decision aligns with your long-term vision. It’s easy to get lost in short-term fires without a clear north star.

Ready to Make Your Next Move?
Let’s be real—navigating growth, strategy, and leadership as a founder isn’t easy, but you don’t have to do it alone. Just like Glen has helped me, I can help you cut through the noise, focus on what matters, and take your business to the next level. Whether you’re scaling, pivoting, or figuring out your next big move, let’s talk about how we can make it happen together.

Schedule a 15-minute chat today.

Glen's best advice for entrepreneurs:
“A plan is just a verb, a noun, and a date. That’s it—get the next thing done, then deal with what comes next.”

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