The Founder's Journey Podcast

How can humble assertiveness transform your leadership style and drive your startup's success? In this episode of the Founders Journey Podcast, Greg Moran, co-founder of Evergreen Mountain Equity Partners, breaks down how this unique leadership trait combining confidence with humility empowers founders to make decisive, impactful choices while fostering collaboration within their teams.

Explore real-life examples of leaders like Evan Williams, co-founder of Twitter, and Jeff Evans, renowned mountain climber, who thrived by balancing assertiveness with humility in high-pressure environments. Learn how you can apply these lessons to lead your startup with greater empathy, decisiveness, and long-term vision.

Key Takeaways:
- What is humble assertiveness, and why is it crucial for startup leaders?
- How Evan Williams used this trait to drive Twitter’s growth
- Jeff Evans’ inspiring leadership on the slopes of Mount Everest
- Practical steps to develop humble assertiveness in your leadership journey
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00:00 – Introduction: Humble Assertiveness in Leadership
00:31 – Defining Humble Assertiveness
01:10 – Why Founders Struggle with Balancing Leadership and Collaboration
02:00 – Example: Evan Williams’ Leadership at Twitter
03:00 – Example: Jeff Evans and His Everest Expedition
05:00 – How to Develop Humble Assertiveness in Yourself
06:00 – Download the Free White Paper
06:20 – Conclusion: Subscribe and Share
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Download our white paper on the behavioral DNA of successful founders to discover the traits that separate good leaders from great ones: Understanding the Behavioral DNA of Successful Founders

Connect with Evergreen Mountain Equity Partners for more insights on leadership, venture capital, and scaling your business: https://emep.io/

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#HumbleAssertiveness #LeadershipTips #Entrepreneurship #StartupSuccess #BusinessGrowth #VCAdvice #FoundersJourney #EmpathyInLeadership #StartupLeadership #DecisionMaking

What is The Founder's Journey Podcast?

Telling the stories of startup founders and creators and their unique journey. Each episode features actionable tips, practical advice and inspirational insight.

00:00:00:00 - 00:00:10:09
Welcome to the Founders Journey podcast. Inspiration education for Founders by Founders.

00:00:10:09 - 00:00:31:14
Hey, I'm Greg Moran, co-founder of Evergreen Mountain Equity Partners and host of the Founders Journey podcast. Today, we're talking about something essential for every leader, and it's one of the traits from our recent research at Evergreen Mountain around the traits that are consistent among top performing founders, startup leaders around the world. That trait today is humblest of us.

00:00:31:15 - 00:00:52:20
So this is an interesting one. This is the ability to lead with confidence while really empowering others to contribute without needing to dominate. It's all hard thing for founders. It's a hard thing for me. I know that and I'm sure you probably struggle with it too. So if you've ever found yourself struggling to balance leadership and collaboration, you're in the right place.

00:00:52:21 - 00:01:21:01
So let's dive in. So humble assertiveness is one of the most important traits for successful leadership. Whether you're a startup founder or you're leader in a larger company, it's really the ability to stay confident in your vision and in your decisions, but also be humble enough to listen and then collaborate and trust your team at Evergreen Mountain. We invest in it's number one thing that we invest in and founder is founders and their ability to lead and their ability to execute.

00:01:21:02 - 00:01:44:20
And we found that the most successful leaders founders that we work with leading in this way, they're sort of when they need to, but they never dominate the conversation. They never dominate the room. They empower their teams to really succeed. So at its core, it's really about balancing leadership with collaboration, knowing when to assert yourself and knowing when to listen.

00:01:44:20 - 00:02:07:18
Shut up. Listen again. Hard thing for a lot of founders, super hard for me. This trait allows leaders to really make strong decisions, but it ensures that the that their teams are feeling heard and they're feeling valued, and they're part of the discussion and it's not coming down on one person's shoulders. So a great example of humble, assertiveness in them is Evan Williams.

00:02:07:18 - 00:02:33:09
So Evan was the co-founder of Twitter and Blogger.com. He's known for his really quiet, understated leadership. He didn't dominate discussions or really go out of his way to seek the spotlight, but he always was clear about the strategic direction you want a Twitter to take or blogger.com. So he built Twitter by really empowering his team to experiment and innovate and giving them the authority to really shape the platform.

00:02:33:10 - 00:03:01:02
Now the platform has obviously changed quite a bit under Elon Musk, but it was really William's sort of vision and leadership that got, Twitter to where it was. And being this global brand. So what he was doing was really balancing assertiveness with humility and leading by example but not micromanaging. So when the time came to step down as CEO, he did so with Grace, demonstrating that his leadership was never about his own personal power, but what was best for the company.

00:03:01:09 - 00:03:22:25
One of the most compelling stories that I have heard personally and somebody I've, I've worked with and had the pleasure of, knowing for a long time and had him speak and things like that is CFO by name is Jeff Evans. He's a world renowned mountain climber and exhibition leader. If you haven't listened to the Founder's Journey podcast with Jeff Evans, do yourself a favor and go listen to it on the channel.

00:03:22:25 - 00:03:43:17
It's one of the best, I think, episodes of the of the podcast of the Founder's Journey podcast, where Jeff shared a story from his Mount Everest expedition that really illustrates this trait. So Jeff and his team were just below the summit of Everest when they hit a really critical point on the path. The weather was turning and the team was exhausted.

00:03:43:17 - 00:04:03:22
And as the leader, Jeff had a really life or death decision to make. Do we push forward or do we turn back? Jeff was a leader and he had to make that decision, and this was the moment of really humble assertiveness that he had a really that he had a face. He was confident, obviously, in his abilities, but he also trusted the team's input.

00:04:03:22 - 00:04:30:08
So instead of making a solo decision, as you often see leaders do, Jeff gathered the team, listened to their feedback, took their safety into account, and ultimately they decided to push forward but with extreme caution. So, thanks to Jeff's ability to balance confidence and humility, his team reached the summit of Everest. His leadership was about knowing when to lead and when to listen, and to involve his team in that, in those critical decisions.

00:04:30:08 - 00:04:52:27
So how do you develop humble leadership? First of all, it can be developed. And how do you develop it in yourself here really a few key steps. Be confident but not controlling. You've got to trust your team, and you've got to trust your team to execute on your vision without micromanaging. You have to listen actively. You've got to make space for others and be open to changing your approach.

00:04:52:27 - 00:05:13:07
Your approach is not always the right one, and having your team involved and truly listening and being open to make changes is critical. You've got to empower your team. You got to give them the autonomy to make decisions on their own, and then trust that they're going to learn from those mistakes that inevitably can happen. But you've got to assert your vision.

00:05:13:09 - 00:05:34:02
You've got to stay clear as a leader on your goals and values, but then remain flexible on how you get there. So humble assertiveness is a is a really crucial trait for any leader. Whether you're running a startup, leading an expedition with Jeff Evans was it allows you to drive your vision forward while empowering your team to succeed.

00:05:34:04 - 00:06:00:15
So if you want to dive deeper into this and the other, traits that define successful leadership from our entrepreneurial adaptive innovator archetype, really interesting. Dig in to download our free whitepaper at MF Geo. That's our website for Evergreen Mountain Equity Partners. MVP, io. Download the white paper Understanding the Behavioral DNA of Successful Founders. And before you go, don't forget to like the channel.

00:06:00:22 - 00:06:19:23
Subscribe. Hit the notification bell so you don't miss future episodes of the Founders Journey podcast, and drop a comment below how do you balance assertiveness and collaboration in leadership? We'd love to hear from you. So thanks again for joining us. We'll see you next time.