Meet Ryan Vaughn - coach, CEO at Inside-Out Leadership. Over 15 years, he founded and led three companies. His last venture, VNN, became the largest and fastest-growing high school sports marketing platform in the US. He raised $20M from leading VCs, building a team of over 100 employees and scaling VNN to capture nearly 20% of the US market. From pitching to scaling and managing hyper-growth, Ryan's lived the full startup lifecycle.

But behind the scenes, Ryan struggled with tying his self-worth to his company's success. After a tough exit from VNN, he set out on a journey of self-discovery and learned to build companies as a true expression of himself. Now, as a coach, he helps other founders navigate the difficulties of startup life and personal growth.

In this episode, Ryan breaks down the mental and emotional battles that many startup founders fight in private. As someone who's been in the trenches myself, I appreciated Ryan's honesty and vulnerability. From burnout to the illusion of control, identity crises, and the power of authenticity, Ryan's journey mirrors the hidden struggles many of us face.

Ready to dive into the hidden mental battlefield of startup life? Listen to the full episode here:

Below, we explore a founder's journey through:

• Recognizing the subtle signs of burnout before it's too late
• The paradox of letting go to gain true control
• Separating your self-worth from your startup's success
• Navigating the identity crisis after exiting a company
• Embracing authenticity as a path to fulfillment

Recognizing Burnout

Burnout is a topic that hits close to home for many of us. It often starts so subtly that we don't realize we're headed for trouble until it’s too late:

I think I felt burned out for a couple of years before I finally left the company. There was anger, frustration, sadness. Near the end, there was an increasing sense of duty – just going through the motions.

We're all guilty of ignoring red flags, aren't we? We get so caught up in the grind that we forget to check in with ourselves. But burnout isn't just a personal issue, it's a startup killer. It messes with our decision-making and can tank the very thing we're killing ourselves to build. For me, learning to spot these signs early was a game-changer. Sometimes, the most productive thing you can do is step away from the laptop, take a breather, and touch some grass.

Letting Go to Grow

Once we recognize it, it often becomes clear that burnout stems from trying to manage every aspect of our business. This leads to one of the toughest lessons for any founder - realizing you can't control everything:

I certainly tried to control every little piece. Because I tried to control everything, any deviation felt like a mortal threat to my competence.

This is the fear that if you're not involved in every little decision, something will go terribly wrong. But here's the thing - the tighter we grip, the more stuff slips through our fingers. Letting go isn't about losing control; it's about empowering your team. When I finally learned to delegate at NeoWork, it was like a weight lifted. Turns out, my team had some pretty brilliant ideas when I got out of their way.

Disentangling Self from Startup

As we let go of control, we then face the even deeper challenge of separating our personal identity from our company's success.

I remember telling my wife, 'I can't convince myself that a bigger company will make me feel any different. I think I'm just running from this feeling that I'm not worth anything.'

How many of us have tied our self-worth to our company's latest valuation? It's a slippery slope. The truth is, you are not your company. Your value isn't measured in term sheets or pitch decks. This realization allowed me to make clearer decisions and, ironically, become a better leader.

Navigating the Post-Exit Void

After achieving success or facing failure, many founders grapple with a loss of identity. Ryan sheds light on this critical phase:

When I left, and actually, I hired my replacement as a CEO and then got in a fight with him and then he ended up having to fire me. So was not a happy leaving when that happened. And all of a sudden, who I am, the CEO of VNN is gone. Can't be that anymore. And I have to reckon with... What does that mean? What goes in that vacuum of identity after you exit a company or whatever way you do it?

When you've poured everything into a company, its absence leaves a gaping hole. The identity we've built as founders suddenly vanishes, and that can be jarring. Ryan reminds us that exits aren't always clean or voluntary. The real challenge isn't just leaving the company; it's figuring out who we are without it. This void is terrifying, but it's also an opportunity for growth, rediscovery, and to redefine success on our own terms.

The Power of Authentic Self-Discovery

As we wrapped up, Ryan spoke to his personal journey after exiting in a way that captured the themes we explored throughout the conversation.

I spent the next 2 years searching, meditating, hanging out with monks, diving into psychedelics, and trying on new identities that never felt right. I was stuck. And then, I finally opened up. I started being honest about my struggles, despite the voice in my head telling me to play a role. I let go of my compulsion to be "Ryan the CEO," or "Ryan the entrepreneur," or even "Ryan the guy who's raised a ton of money and scaled a media company." I was just, Ryan.

It's the perfect summation of the founder's journey we've explored - from recognizing burnout to letting go of control, from separating our identity from our startup to embracing vulnerability. At the end of the day, our most powerful tool as leaders is our authentic selves. It's not the titles we hold or the metrics we chase, but about showing up as ourselves, struggles and all. When we do this, we not only find personal fulfillment but also create space for meaningful connections within our teams and companies.