Simplus CEO Ryan Westwood

Today, Ryan Westwood is widely regarded as the entrepreneur's entrepreneur, often commiserated by other entrepreneurs, and a leader respected in the field. What makes Westwood unique is his ability to move from dream to reality and how he uses the journey to propel others forward. He understands that his business success is built on his empathy for his peers' success.

So, what is the most important characteristic a leader of entrepreneurs should have? Westwood says it boils down to understanding that success isn't all about oneself. "When I think of myself as an earlier leader, I was worried about me and how I would develop; I was worried about what other people thought of me," Westwood reflects. "But after we sold Simplus, it was like this moment where I walked out of the arena, and I'm like, 'I no longer care what any of those people think; I care if I make an impact.'"

Westwood learned early on that what you believe is holding you back probably doesn't exist. He implemented mediation to combat self-sabotaging beliefs about himself and his trajectory. "I would say with maturity, sometimes we say things just because we want people to hear us," he said. "We want to be heard, and we want to lead, not because it is beneficial to those people," noting the importance of taking in the advice of others to a certain extent, but discerning which advice is ultimately best for you and your business, and which can be left aside.

Knowing how and when to allocate your attention is a crucial lesson Westwood has been able to refine with time. He recommends falling back on tactics such as the V2MOM methodology to help entrepreneurs understand how to organize their priorities and manage their time efficiently. However, Westwood has been able to take it a step further by applying what he learned from the journey and using it to fuel his current career and the next generations of entrepreneurs. Westwood states, "I think that there's great skill in extracting from others, from their journey, lessons learned, applying them to yourself; that's a real skill."

Westwood's experience in the entrepreneurial world has taught him the importance of going deep on the lessons we take away from the journey rather than disregarding them for convenience. He is also a staunch advocate of innovation in the capital-raising process. He recommends entrepreneurs take a more pragmatic approach by pushing aside their frustration with venture capitalists and instead question them to learn more about their funds, their check sizes, and what a board seat or observer seat entails. Westwood got his start in this arena while leading the UVEF, an organization encouraging entrepreneurs in the Utah area.

Ultimately, Westwood says the most helpful insight he's gained through the process is entrepreneurs and venture capitalists are equally competitive. No venture capitalist wants to miss the subsequent big success and be reminded of the one that disappeared.

With experience, Westwood has incorporated this understanding into his fundraising approach. He has continued to shake up the industry, finding additional sources of capital outside the venture world, utilizing his employees' money, and tapping into the line of credit for venture debt. He employed a $50K minimum investment on his executive leadership team. He found that their hearts were committed to the vision in an incredibly beneficial way for the capital-raising process.

Westwood learned that the moment you understand it isn't about you but about those around you, you can move forward advantageously for everyone. He urges entrepreneurs to lean into the journey, noting, "Leaders should be looking at the journey and making sure they are providing the environment to maximize the learning and creating an environment where there is room for failure."

Westwood's experience offers a roadmap for leading effectively and growing holistically. He encourages entrepreneurs to think in a less traditional way to generate the success they desire. In the face of adversity, Westwood has fortified a remarkable career stemming from his willingness to re-frame the lens through which leaders perceive themselves.