Greetings, Chief Storytelling Officers.

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On Friday I turned 36.

Today I want to share a story with you. It's my story. Not the perfect Hollywood version. The real one.

Next week, I'll be back with our normal deep dive on storytelling and fundraising for founders and entrepreneurs.

This week, we're going meta. The lesson in storytelling is in the storytelling.

Before I start, thank you. Thank you for trusting me. Thank you for reading this each week. Thank you for investing your time and attention. Thank you for showing up.

-Robbie

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DEEP DIVE: It's been a hell of a ride

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The head of the child abuse unit looked at me shocked when I told her I was done being a prosecutor. She told me about the leadership team's plans for me inside of the office and asked me to reconsider, but I knew I couldn't.

I loved that job. Putting abusers behind bars and protecting child victims of physical and sexual abuse gave me a deep sense of purpose and pride. But it was a dark world to live in every day.

To this day I still think about the cases, the families, and the victims. Many of them will haunt me forever but that was my job. To take that on. Until I knew I'd reached the end. So I left it all behind to chase that dream I'd had since I was much younger.

I wanted to be an entrepreneur.

Growing up I watched my dad turn a temporary position into a permanent one-man role at an oil company in Houston. The one-man role kept growing and I had a front row seat. He was my baseball coach until high school. So I heard his calls in the car, saw how he negotiated deals, and always asked him to tell me stories about his travel and work.

He eventually became the Vice President of global real estate. That means he ran a PnL of over a billion dollars with a team in the thousands.

I wanted to be like my dad.

The way I ended up as a trial lawyer first is simple. It made my parents proud that they had a lawyer in the family and I knew I would find a way to leverage it at some point down the line.

I never knew how, I just knew that I would figure it out.

So when I left the DAs office, I set out to learn how to build a business and then do it.

I didn't know a single founder. I didn't know a single venture capitalist. I didn't know a single thing about tech.

But a few years earlier, I'd seen the show Silicon Valley. I watched the characters on that show and saw where my skills could make a difference. I couldn't code. I couldn't build software or some app. But I was one hell of a storyteller.

This led me down the path to market research.

I used my legal research background plus my background as a history major at Haverford College. I looked at trends and leaned into all the time I'd spent on understanding narrative control, messaging strategy, and storytelling.

What I saw is that this generation's change makers are founders working in the technology space but they needed help selling that vision to a skeptical and confused world.

That's where I knew I had something to offer.

So I started by building an edtech. It wasn't sexy. It was built on no-code, duct taped together, and yet it somehow worked. Well it worked as a proof of concept.

To build it, I burned through my entire savings and put everything else on my credit cards. I quickly built up some serious debt.

I've never seen a credit score free fall in such an epic way.

I had no idea what I was doing but I talked to hundreds of potential customers to learn their needs. I spent more time on zoom calls than seems possible looking back. It was me and my dog Roxie working to build something out of nothing.

She kept me company. For that first year, she saw the worst days. The days I didn't know if I could pull it off. The days I thought it might all come crashing down. Roxie is the most important part of this story, you probably don't know.

One day, I'll write a book about our adventures. She was a beautiful english cream golden retriever. I rescued her when she was 5.

2 years ago she passed at the age of 15. Two months after the edtech was acquired, she moved on. Without her, I wouldn't have made it happen. She was the best dog a guy could ever ask for.

So the edtech made it to acquisition. Was it life changing money? Nope.

Was it life changing? Yes.

I'd built something and a large Series B tech company acquired it. I'd found a way to kick open the door to the tech world.

Ever since, I've been building the company I run today called Competitive Storytelling.

In fall of 2021, I didn't know if we'd make it.

I had made a couple of bad moves. I overestimated how easy it would be to change business models and I'd trusted someone outside of the team to deliver in a big way. I wanted a shortcut.

It's why it blew up in my face. There aren't shortcuts.

I ended up having to ask my chief of staff to defer his salary for two months, I had to scramble to find revenue to stay alive, and I had to let go of an employee I knew I'd failed in setting him up for success as I was in survival mode.

As a founder, it felt awful.

I could sweep this all under the rug and paint the pretty picture for you, but that's not the truth.

Straight up, I failed in my role.

But we survived.

By going through that test and hitting what felt like rock bottom, I remember telling my chief of staff that the only place to go from there was up. It couldn't get any worse.

By the end of 2021 we'd figured out our mistakes and fixed them.

That's when I decided to really start posting content on LinkedIn. I wanted to share the ideas and lessons I learned in my work with founders.

The rest has been history.

Is there more to the story?

Of course. I could give you the story of the past year but the short version is that things have gone really well.

That first year with the edtech and the second year almost losing Competitive Storytelling taught me more lessons than I care to count. I lived in chaos and uncertainty for two years. It reminded me of being in a trial. The best trial lawyers loved chaos.

I loved chaos. I still do.

But it can also take a toll.

I withdrew from friends. I was less present with my family.  My bed had one pillow. I lived a pretty boring and lonely life.

When people would ask me why, I'd always tell them because I know if I work my ass off for two years, I can make it worth five years and set myself up for the rest of my life.

I don't know why I believed that, but I did.

Somehow, it's worked.

That being said, it still hurt people and that part sucks. I had to be selfish, or at least that's the story I tell myself now to justify it.

I'm not perfect.

I'm a guy that wants to make a massive impact in this world, build generational wealth, and leave a legacy. That doesn't come without sacrifice and I know that.

So maybe this resonates with you and maybe it doesn't. It's the messy story. The one I think more people should share. Because this entrepreneur stuff is hard but it's also worth it for the right type of people.

I love every day of my work. I wake up excited to get after it. I have a chance to do something extraordinary. I don't take that for granted.

So as I look ahead, I think in a 5 year time horizon because at that point I'll be 40. It's going to be filled with compounding benefits and results.

I'm building the most important communication and storytelling company for the next generation.

The ripples will spread far and wide. The story will grow and I'll share it openly.

Because at the end of the day, I'm a storyteller.

It's who I am. It's who I've always been.

It's how I'm going to change the world.

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RESOURCES for Founders and Storytellers

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I've been super impressed recently with Justin Gordon's newsletter that's doing deep dive storytelling on some of the best founders. He's done them on Sam Altman, Melanie Perkins, and Tope Awotona. I'm a reader and for founders and storytellers, this is a no brainer to read.

FINALLY...

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"In order to have the great meals in this life, you have to be open to the possibility that you're gonna have a bad one." -Anthony Bourdain (RIP to my all time favorite storyteller)

If you're here, why not subscribe to my YouTube channel where I post multiple videos every week on storytelling, entrepreneurship, and fundraising?

See you next week.

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