By Jarred Kessler
Raising capital is one of the most exciting yet daunting challenges for any entrepreneur. The ability to convince investors to believe in your vision, back your strategy, and put their money on the line can mean the difference between an idea that never takes off and a company that changes the world. Over the course of my journey as a founder and CEO, I have had the opportunity to raise $150 million in startup funding from some of the most prestigious investors. It was not easy. The process was filled with setbacks, lessons, and breakthroughs.
I want to share some of the most important lessons I learned along the way. These insights apply to any entrepreneur who is trying to secure capital in today’s highly competitive environment.
The Power of Storytelling
Numbers matter, but stories inspire. When investors evaluate a startup, they are looking for more than financial projections and spreadsheets. They want to believe in the bigger picture. What problem are you solving? Why does it matter? Why are you uniquely positioned to solve it?
The story you tell should connect emotionally with investors while also showing them a path to profitability. In my experience, it was not enough to explain the mechanics of the business. I had to paint a picture of the future and make investors feel like they were part of building something transformative. When you can blend data with vision, you create a narrative that investors cannot ignore.
Building Trust Through Transparency
One of the biggest mistakes founders make is trying to present a flawless picture to investors. The truth is that no startup is perfect. Every business faces challenges, risks, and unknowns. Investors know this. What they want is honesty and transparency.
I learned early on that admitting challenges and showing how we planned to address them built far more trust than pretending everything was smooth. When investors saw that I had a realistic grasp of the risks and a strategy for managing them, their confidence grew. Transparency does not weaken your pitch; it strengthens it.
Relationships Matter More Than Transactions
Capital raising is not just about the money. It is about building long-term relationships. Some of the investors who supported me did so not just because of the business but because of the trust and rapport we built over time.
This means that raising capital is not something you do only when you need money. It is a constant process of networking, building credibility, and nurturing relationships. Investors want to know the person behind the company. They want to know your values, how you lead, and how you respond under pressure. The stronger the relationship, the easier it becomes to secure support when you need it most.
Resilience Is Non-Negotiable
Rejection is part of the process. For every yes, there are usually dozens of no’s. Early on, I took rejection personally. I thought a “no” meant my idea was not good enough. Over time, I realized that rejection often has little to do with you and everything to do with timing, strategy, or the investor’s focus.
Raising $150 million required resilience. It required the ability to hear “no” and keep refining the pitch, adjusting the strategy, and moving forward. Investors respect founders who do not give up after setbacks. In fact, how you handle rejection often tells them more about your potential as a leader than how you handle success.
Understanding Market Timing
Even the best idea can struggle if the market is not ready. Timing plays a critical role in fundraising. Investors are constantly scanning for trends, opportunities, and signals that align with larger market movements.
When I raised capital, part of the challenge was aligning my vision with what investors believed was next. This required me to understand not only my own business but also broader economic and industry trends. Founders who can connect their startup to bigger market shifts have a much better chance of attracting serious capital.
The Right Investors Matter More Than the Biggest Check
It can be tempting to chase the largest check or the fastest deal. However, the wrong investor can create more problems than solutions. The right investors are partners who share your vision, understand your mission, and bring more than just money to the table.
Some of the most valuable investors I worked with contributed advice, industry connections, and credibility that money alone could not buy. Choosing investors who align with your values and long-term strategy is one of the most important decisions you can make.
Turning Capital Into Growth
Securing capital is only the beginning. What matters most is how you deploy it. Investors expect you to transform their funding into measurable growth, whether that means building teams, developing products, or scaling operations.
The discipline you show in managing capital can define your reputation as a founder. In my own experience, being meticulous about how every dollar was used not only strengthened my company but also gave investors confidence to continue supporting me in later rounds.
Final Thoughts
Raising $150 million in a competitive market was not easy, but it taught me lessons that I carry into every venture. Capital raising is about vision, trust, resilience, and relationships as much as it is about money. It requires founders to be storytellers, strategists, and leaders who can inspire confidence even in uncertain times.
For entrepreneurs navigating this journey today, remember this: investors are not just investing in your business. They are investing in you. Your ability to communicate vision, build trust, and execute with discipline will determine not only whether you secure capital but also how far your company can go.