Entrepreneurship Unfiltered: The Truth About Winning and Failing in Startups

By Karry Kleeman
3x SaaS Exited CRO | Board Member | Investor | Advisor | GTM Executive

The Reality of the Founder’s Journey

Building a company from the ground up is one of the most exhilarating, rewarding, and, at times, brutal experiences a person can go through. It’s a journey filled with bold ideas, relentless execution, and the constant need to adapt. As someone who has spent decades scaling businesses—watching companies rise, stumble, and rise again—I’ve seen firsthand what it takes to navigate the highs and lows of entrepreneurship.

If you’re a founder—or dreaming of becoming one—know this: the road ahead isn’t linear. It’s a rollercoaster of wins, setbacks, breakthroughs, and lessons. The key is learning how to manage the turbulence and keep pushing forward.

The Highs: Moments of Triumph

Let’s start with the moments that make the struggle worth it.

1. The Spark of a Great Idea

Every startup begins with an idea—a product that solves a problem, a service that meets a need. That initial spark is electric. You’re fueled by passion and possibility, convinced you’ve found something that can make a real impact.

2. Early Wins and Market Validation

Few things compare to the thrill of seeing your idea resonate with real customers. That first sale, the first wave of users, and those initial positive reviews serve as validation that you’re onto something.

3. Scaling and Growth

As momentum builds, your startup starts to scale. Maybe you raise a successful funding round, expand your team, or see revenue skyrocket. Growth is addictive, and during these moments, it feels like nothing can stop you.

4. Building a Team and a Culture

One of the most fulfilling parts of being a founder is surrounding yourself with like-minded people who believe in the mission. Watching your team grow, innovate, and push the company forward is incredibly rewarding.

5. A Successful Exit

Whether it’s an acquisition, IPO, or another strategic milestone, achieving a significant exit is the ultimate validation of years of effort. But make no mistake, it’s not just about the financial reward—it’s about knowing you built something meaningful.

The Lows: Facing the Challenges

With the highs come inevitable challenges that test your resilience.

1. The Uncertainty and Self-Doubt

There will be moments when you question everything—your idea, your leadership, and even your ability to keep going. Imposter syndrome is real, and even the most successful founders have battled it.

2. Financial Struggles and Fundraising Woes

Cash flow issues, failed fundraising rounds, and tight budgets can bring even the best startups to their knees. Many founders spend more time chasing capital than actually building their businesses.

3. Hiring the Wrong People

Your startup is only as strong as the people behind it. A bad hire—especially in key leadership positions—can set the company back months or even years. Worse, toxic hires can erode culture and morale.

4. Market Shifts and Unexpected Roadblocks

Maybe a new competitor emerges. Maybe your industry changes overnight. Maybe a global crisis like a pandemic turns your business model upside down. The best founders learn to pivot, but it’s never easy.

5. Burnout and Personal Sacrifices

The mental and physical toll of being a founder is often underestimated. Long hours, financial stress, and the pressure to deliver can strain personal relationships, impact health, and lead to burnout if not managed properly.

Navigating the Ups and Downs: Lessons for Founders

So how do you keep going when the journey gets tough?

1. Embrace the Process

The ups and downs are part of the game. Every setback is a lesson, every challenge an opportunity to improve. The founders who succeed are the ones who commit to the journey, not just the destination.

2. Surround Yourself with the Right People

Build a strong network of mentors, advisors, and fellow founders. Entrepreneurship can be isolating, but having the right people in your corner makes all the difference.

3. Be Relentlessly Customer-Focused

Companies that survive aren’t the ones with the flashiest marketing or biggest funding rounds. They’re the ones that obsess over solving real problems for real people. Listen to your customers. Adapt. Iterate.

4. Master the Art of the Pivot

Flexibility is a founder’s superpower. Be willing to shift, evolve, and pivot when necessary. The most successful companies today rarely look exactly like they did when they started.

5. Take Care of Yourself

You can’t build a great company if you’re running on empty. Prioritize your health, relationships, and mental well-being. The startup grind is real, but burning out doesn’t make you a better leader—it makes you ineffective.

Final Thoughts: Keep Moving Forward

Entrepreneurship is not for the faint of heart. It’s for those who are willing to take risks, endure setbacks, and keep pushing forward. If you’re on this path, remember: the highs are worth celebrating, and the lows are worth learning from. The best founders don’t just survive the journey—they embrace it.

So keep going. Stay resilient. And most importantly, enjoy the ride.

About Karry Kleeman

​​Karry Kleeman is a seasoned software executive, go-to-market strategist, and revenue leader. He thrives at the intersection of business growth and human connection, blending a sharp instinct for scaling companies with a deep passion for people and a commitment to infusing a human touch into the process. He is known for bringing energy and clarity to organizations—rallying teams around a common mission, driving execution, and creating momentum that fuels growth.

With a career spanning decades in enterprise software, Karry has built and led high-performing revenue organizations from early-stage startups to IPOs and strategic acquisitions. He has played a pivotal role in scaling multiple companies to successful exits, generating well over $1 billion in enterprise value. At LogicGate, he architected a go-to-market strategy that propelled the company from $1M to $50M in ARR. At SpringCM, he led the revenue function through its $270M acquisition by DocuSign. And at Mobius he helped scale the business from $3M to over $100M, culminating in a successful IPO.

Karry’s ability to inspire and energize teams is a core part of his leadership. Just as he commands attention and engagement when performing live music, he brings the same presence and intensity to leading teams—aligning them around a shared vision, setting the pace, and ensuring everyone is moving in rhythm toward ambitious goals. When he’s not driving business growth, you’ll find him performing classic rock hits anywhere he can find a live mic.