Most founders survive storms. Few know how to leverage them.

The setbacks, missteps, and near-disasters you would rather skip are often the very moments that give your story weight.

But as a founder, you need to know these storms you survived are not liabilities. They are assets waiting to be shaped.

In this issue, I'll show you why bad experiences create unforgettable stories, how vulnerability spreads influence, and how to turn one difficult moment into a reusable storytelling asset. You'll also get:

  • 5 founders who turned hard moments into trust-building tools

  • 3 ways to convert one vulnerable moment into a reusable storytelling asset

  • 1 video that shows how vulnerability builds trust and influence in real time

Enjoy the storm, it looks good on you….LG

Founder Story Tip: Learn To Love The Storm

Last year, Austin had a massive snow storm that shut down the city so I went to the park and did some lawn art and made snow angels

If you are building a company, storms are guaranteed.

Failures will happen. Setbacks will test you. Moments will arrive that shake everything you thought you knew.

The question is not whether those storms will come.

The question is: Will you learn to use them?

Because here is the truth most founders miss: bad experiences can make for great stories. And great stories build trust faster than any credential, any traction number, any polished pitch ever could.

When you share struggle authentically and with purpose, people do not see weakness. They see themselves.

That recognition creates empathy. Empathy builds trust. And trust is the currency of everything you are trying to build.

This issue breaks down how to turn your hardest moments into your strongest stories. How to leverage vulnerability strategically. How to make the storm work for you instead of against you.

VULNERABILITY IS THE GATEWAY TO CONNECTION

Here is what most founders miss: when you share struggle, people do not see weakness. They see themselves.

That recognition creates empathy. Empathy builds trust.

And trust is the currency of influence.

If you want people to follow you, support you, believe in what you are building, write you a check, or join your team, they need to trust you first.

Vulnerability accelerates the trust process.

As we covered in a previous issue on embracing vulnerability, vulnerability includes uncertainty, risk, and emotional exposure. That is what scares founders.

But with that foundation in place, understanding that vulnerability is not weakness but strategic honesty, we can now focus on how to leverage it.

Vulnerability creates the emotional doorway between you and your audience. Without it, the door stays closed. With it, people step through and lean in.

When you share authentically, you signal honesty. You are telling the truth, even when it is hard. You signal self-awareness. You know what you did not know. You signal confidence in your path. You are not hiding from your journey. You signal comfort with who you are. You have made peace with the mess.

That combination reads as credible, not risky. As strong, not weak.

Carley Roney transformed a personal nightmare into the catalyst for The Knot. Her wedding planning experience was chaotic and overwhelming. Instead of hiding the mess, she openly shared her frustration, stress, and disappointment, then used that moment to identify a real unmet need.

By starting with a vulnerable personal problem, she created a brand rooted in empathy and usefulness. Her story works because it starts with honesty and leads to purpose, helping her build a $130 million brand.

BAD EXPERIENCES MAKE GREAT STORIES

The most memorable stories begin with something going wrong.

Our brains are wired to notice danger and uncertainty. Crisis commands attention. Struggle creates emotional weight. Failure introduces tension, stakes, and contrast that draw people in.

Gary Keller did not hide his mistakes from scaling Keller Williams too fast, and that honesty helped him build the largest real estate company in the world.

Clayton Christopher openly admitted what he did not know building Sweet Leaf Tea, which helped him create a brand that sold for nine figures.

These founders recognized that perfect paths feel artificial and forgettable. Easy wins fade quickly. But when something goes sideways, audiences lean in because they want to know what happens next.

Reframe your thinking and understand that bad experiences:

  • Give your story conflict, the engine that drives narrative forward

  • Create contrast, making the gap between before and after visible

  • Build credibility because you earned your perspective through experience, not theory

  • Create connection in that people relate to struggle more than success

Stories rooted in difficulty stick in memory longer because emotion strengthens recall. Audiences remember moments of risk, loss, and recovery more vividly than smooth success

VULNERABILITY IS CONTAGIOUS

Here is the ripple effect: when one person opens up, it creates permission for others to do the same.

It accelerates trust far faster than guarded professionalism. It creates advocates who feel personally invested in your success.

One story often invites another. Barriers come down quickly. Empathy grows on both sides.

When you go first with vulnerability, you give others permission to be human too. That is influence.

This is exactly what I saw Brené Brown, one of the world's foremost experts on vulnerability, demonstrate with 200 of the country's top CEOs and founders at the Conscious Capitalism CEO Summit. I was filming the event and interviewing the CEOs when Brené gave her keynote.

When she went first and shared her own struggles with leadership and vulnerability, the entire room shifted. Leaders who had spent their careers projecting certainty suddenly felt safe enough to admit doubt, fear, and uncertainty.

That is the contagion effect. Vulnerability invites vulnerability.

Sara Blakely made failure a central part of her story and her pitch for Spanx. She openly shares rejection from manufacturers and retailers. She talks about embarrassment, self-doubt, and early missteps. She celebrates failure as proof of effort. Blakely regularly credits her comfort with failure as a competitive advantage. 

By making rejection visible, she removes fear from the process. That honesty makes her story memorable and makes success feel earned, not lucky, and became a powerful force that helped her become the youngest self-made female billionaire in history.

TURN BAD INTO GOOD: MAKE IT HUMAN

Embrace the storms like kids dancing in fountains

To use vulnerability strategically, you need to convert what happened into meaning your audience can feel and apply.

This is not about glamorizing pain. It is about turning lived experience into a story that teaches, connects, and builds trust.

The goal: Share the scar, not the wound.

Share what healed and what you learned, not what is still bleeding.

Brian Sharples, founder of HomeAway, openly credits failure as his greatest teacher. He talks about early failures and missed opportunities. He frames setbacks as shaping moments, not regrets. He refers to this process as learning from the storm.

By sharing what went wrong and how it changed him, he builds credibility with other founders. His story resonates because it treats failure as a shaping force, not a liability, and that perspective and those learnings helped him turn HomeAway into a $3.9 billion exit.

USE THE STORM

Storms are coming. They always are when you are building something that matters.

But use these storms as story material.

The failures, the embarrassments, the moments that almost broke you, those are the stories that will connect you to your audience faster than any perfectly polished narrative.

Learn to love the storm. Chronicle it. Mine it for lessons. Make it human. Use it to build trust.

Because when you stop hiding and start sharing the truth, you shift from performing to leading. And that is when people start following.

Storytelling Lessons: Turning One Vulnerable Moment Into a Reusable Asset

If you have already done the work of naming your disasters, finding the human moments, and identifying your contrast from the previous issue on embracing vulnerability, you are ready for this next step. If not, start by acknowledging what went wrong, what it felt like, and how you changed because of it.

Now let's take one vulnerable moment and turn it into a strategic story asset you can use. Here is the three-step process:

  1. Chronicle the Event Clearly

    Pick one difficult experience from your founder journey. Map the sequence cleanly.

    Start with context. What was happening before that moment? Then describe what happened. Be specific. What broke? What went wrong? Capture how you felt. Fear? Shock? Embarrassment? Then show what happened after. What were the immediate consequences?


    Keep it specific, but keep it moving. Do not get stuck reliving every detail. Think 60 seconds when told out loud. Write it out in 4 to 6 short sentences. Read it aloud. If it drags, cut.

  2. Mine for the Insight That Matters

    Raw experience is not enough. The power is in what you learned.


    Ask yourself: What surprised you about this experience? What did you misunderstand at the time that you see clearly now? What assumption got shattered? The insight transforms complaint into connection. It shows growth and self-awareness.


    Write 2 to 3 sentences answering: What is the one thing I understand now about myself, my business, or my leadership because of this experience? Make it specific. Make it honest. Make it useful.

  3. Balance Vulnerability with Value

    Here is where most founders get it wrong. They either share too much raw emotion with no lesson, or they jump to the lesson too fast and lose the human connection.


    The ratio that works: for every 2 sentences of struggle, include 1 sentence of learning. Too much struggle without insight reads as complaining. Too much insight without struggle reads as preachy.


    Show what the experience felt like. Let people into your internal world: the fear, the doubt, the decision point. Then connect it to growth. What changed in you or your approach?

Video to Watch: 

In this video: “Vulnerability. The Gateway Drug to Connecting With Audiences When Sharing Your Story”, I unpack why vulnerability is not weakness, but leverage. It makes you human. It makes you relatable. It builds trust faster than polish ever will. It signals courage and confidence. And when you share honestly, others often follow. If you want audiences to lean in instead of tune out, this is the shift that changes everything. Watch here:

Need help with your story? I got you.

Send an email to [email protected] and someone from my team will circle back with you.

Storytelling for Entrepreneurs Issue #072-🤔 The One Asset Most Founders Refuse to Use

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