Jarred Kessler is a visionary entrepreneur and leader known for turning complex challenges into opportunities for growth. With over fifteen years of experience in finance, technology, and operations, he has built a career defined by innovation, adaptability, and impact.
As the CEO and Founder of EasyKnock, Kessler transformed the way people think about homeownership and financial freedom. His idea was simple but powerful — help homeowners access their home equity without giving up their homes. Under his leadership, EasyKnock grew quickly, earning national attention for combining technology, empathy, and real-world problem solving.
Before EasyKnock, Jarred Kessler worked in financial services, where he learned to navigate fast-changing markets and use technology to create better systems. He later founded Momentum Advisors JBK, helping other founders scale their businesses, raise capital, and turn vision into reality. Throughout his career, he has raised more than $150 million from top investors and advised startups on how to grow with purpose and precision.
Kessler’s leadership style is clear and focused. He believes great leaders don’t just set goals — they build teams, simplify problems, and inspire progress. His work bridges the worlds of finance and innovation, showing how adaptability and strategy can create lasting success.
Driven by curiosity and a belief in the power of change, Jarred Kessler continues to shape industries and inspire entrepreneurs. His story is one of vision, resilience, and the drive to make business work better for people.
Q&A with Jarred Kessler: Redefining Success Through Change and Vision
How do you define success?
Success isn’t a straight line — it’s a series of pivots. It’s not about titles or money; it’s about creating something that didn’t exist before and seeing it make a real difference. Early in my career, I used to chase outcomes — the next role, the next deal, the next win. But over time, I realized success is about the process. It’s how you think, how you adapt, and how you lead when the plan doesn’t go your way.
When I built EasyKnock, it came from seeing a gap — homeowners who were asset-rich but cash-poor. Success, in that case, wasn’t about profit. It was about helping people stay in their homes. That’s the kind of win that lasts.
What’s one lesson you’ve learned from failure?
Failure is data. Early in my career, I saw failure as an ending. Now I see it as information. When you lead companies through volatile markets — like I did in finance and later in real estate — you learn that every misstep is a signal.
When I was scaling EasyKnock, we made decisions that didn’t pan out. We hired too fast in one department and underinvested in another. Instead of pointing fingers, we analyzed what the data was telling us and adjusted. That kind of disciplined flexibility is what keeps businesses alive. Success isn’t avoiding mistakes — it’s learning faster than your competitors.
You’ve led companies through major change. What’s your approach to leadership in uncertain times?
Leadership during uncertainty comes down to clarity. When markets shift or strategies need to evolve, people look for direction. The best leaders simplify chaos — they translate uncertainty into action.
At Momentum Advisors JBK, I work with founders who are often overwhelmed by complexity — too many moving parts, too much pressure. I always tell them: “Start with what you know. Define the problem clearly. Then move forward in small, informed steps.”
You can’t predict everything, but you can control how you think. That’s leadership — not control, but clarity.
How has technology shaped your view of success?
Technology is the great equalizer. It doesn’t care about hierarchy or history — it rewards innovation. I’ve seen entire industries shift because someone used technology differently.
In finance, I noticed how automation and data analytics were changing the way we manage risk and build products. That’s part of what inspired me to create new financial models that were more flexible and human-centered.
Now, AI is changing the game again. But I don’t see it as a threat to leadership — I see it as an amplifier. The leaders who will succeed are the ones who know how to pair technology with empathy. Machines can process data, but only people can interpret it through the lens of purpose.
What advice would you give to young entrepreneurs chasing success?
Start by defining what your success looks like — not what you think it should look like. Too many founders chase validation instead of vision. If you’re building something just to raise money or make headlines, you’ll burn out fast.
When I raised $150 million in startup capital, it wasn’t about the number. It was about aligning the right people with the right mission. That’s what sustains you when things get tough.
Also, learn how to listen. The best entrepreneurs don’t talk the most — they absorb the most. Every customer complaint, every investor question, every piece of feedback is a gift.
What’s one thing people misunderstand about success?
That it’s glamorous. It’s not. It’s a grind. Behind every “overnight success” is ten years of building, adjusting, and staying the course. People often see the outcome but not the process.
When I was transitioning from finance into entrepreneurship, I had to unlearn a lot — like how to operate without a safety net. Success often means being uncomfortable, and that’s okay. Discomfort is a sign you’re growing.
How do you stay motivated after so many years in high-pressure industries?
I stay curious. The moment you think you know it all, you stop learning — and that’s when you start falling behind. Every few years, I try to reinvent the way I think about business. That’s why I’ve worked across finance, real estate, and technology.
I get motivation from solving hard problems. The tougher the challenge, the more creative you have to be. And when you can build something that helps others — that’s fuel for the long run.
What does success look like for you today?
It’s about impact and legacy. I want to keep creating value — for customers, founders, and industries. But beyond that, I want to keep learning and growing. Success isn’t a finish line; it’s a mindset.
At this stage, I measure success by the problems I help solve and the people I help grow. Everything else — the titles, the exits, the metrics — those are just milestones. The real win is staying true to what drives you.