Wear your entrepreneurial scars with pride

3 ways to make your vision a reality—and survive to tell the tale

February 27, 2023
min read

Greetings, Chief Storytelling Officers.

The majority of readers of this newsletter are founders who are looking for ways to become world-class storytellers and also fundraise huge rounds of venture capital.

This week I put together a step by step playbook for raising your series A.

You can find the video here.

Over the past few weeks, we've had a number of our founders close out their rounds. Three just finished and we have two others that are closing out their rounds.  

Why do I tell you this?

Because our Founder Fundraising Program works and that YouTube video will help you set up your own successful series A.

Now let's get to the deep dive.


DEEP DIVE: Learning To Swim

Shortly after I left my career as a trial lawyer, I had big dreams. I knew I wanted to answer one question: How could I help people with world-changing ideas, communicate those ideas to change the world?

I immediately had my North Star. The problem was, I didn’t know how to get there.

I decided to build an edtech startup without any idea how to do so. I didn’t know how to code, I didn’t know anybody in tech. I didn’t know anything—except the vision that I had in my head.

I was CERTAIN I could help people.

While building the company, I felt like I was fighting to just keep my head above the water a lot of the time. It was difficult and awkward. But I kept going. I built and grew it piece by piece. I built a website. I talked to hundreds of potential customers. I even pre-sold before I started building.

I also maxed out credit cards and was filled with the extreme highs and lows of the founder journey.

Eventually, we hit product market fit and I ended up exiting it through an acquisition at the end of 2020. Which means I even figured out how to negotiate that type of a deal (the lawyer thing came in handy).

The thing about the entrepreneurial landscape is that by its nature, you’re rarely going to have a blueprint to follow. You're going to get cut, bloodied, and bruised. It's hard. Really hard.

The lack of structure can be scary and overwhelming, and it causes many weaker founders to get frustrated and quit—or worse, play it safe and end up just another copycat startup in the middle of the heap.

When faced with wide open spaces and infinite choice, we often default to doing things the way we’ve been taught. When it comes to charting our course, that means we tend to expect a linear progression. There’s a reason we compare our career paths to a ladder—we think it will take us one rung at a time until we reach the sky.

That might be the way it works in the corporate world—though many would argue that landscape is changing as well—but it’s certainly not true of the startup space. Achieving your vision is more like a game of Frogger—what will feel like lateral or backwards moves are just steps you need to take in order to not get squashed by oncoming traffic.

It takes some work to get comfortable with that mindset shift, because it’s going to feel like you’re not totally in control.

To help you get there, here are three areas to focus on when you feel like you’re over your head:

Learn The Landscape

While my first startup ended up with a successful exit, I knew that I still had a lot to learn. I realized I needed to figure out what it looked like to scale quickly.

To do that, I joined a growth-stage startup as employee #48. I watched everything they did—how they ran meetings, how they used different software to scale quickly, how they recruited talent, and how they messaged for future fundraises.

When it comes to building your business, this type of experiential learning is critical. Shift your perspective on where you currently are in your journey. Rather than seeing your current position as a dead-end or stall point, focus on the knowledge and experience you’re collecting. What can you learn from your current environment that can help you further your own journey?

It’s kind of like how Harry Potter went on a journey to collect Horcruxes. In order to defeat Voldemort, he needed to go on seven different missions. It would have been impossible for Harry to defeat Voldemort without first destroying the Horcruxes.

Know When To Delegate

Red Adair was one of the most famous firefighters of all time. During his career, he battled more than 2,000 land and offshore oil well fires, and the 1968 John Wayne movie, Hellfighters, was loosely based on his life.

Adair was also good for advice, including this nugget of wisdom: “If you think it’s expensive to hire a professional to do the job, wait until you hire an amateur.”

What that means to me is yes, you should absolutely learn everything you can about each aspect of your business, but it’s also important to know when to ask for help. Sometimes, surrounding yourself with experts is the smartest move.

During my journey building the edtech and now building Competitive Storytelling, I've spent well into 6 figures to speed up my learning curve. When I combined that with insane hours I put in for two and a half years, the hyper growth we've seen was inevitable.

As entrepreneurs, we often feel obligated to put our stamp on everything. It’s part of the bootstrap nature of startups. But as things start to pick up steam, we can quickly get in over our heads, and our unwillingness to bring in an expert can actually hold us back.

For example, you might be a QuickBooks whiz, but as your company grows you’ll never be able to match the skills of an experienced CFO who’s scaled a company to where you want to be. Or maybe you’ve got the basics of storytelling down, but you need an expert to really hone in on your company’s messaging to increase your valuation or make sure you don't miss out on that next round of funding.

Asking for help and admitting your shortcomings isn’t a sign of weakness. It takes courage to do that. And the best part? Once you see up close and personal what these experts do, you’ll never lose that knowledge. You’ll carry it with you on the next step of your journey.

Dive into the Deep End

While gathering intel and surrounding yourself with experts is important, the time is going to come where you have to jump.

Six months after I joined that scaling startup I mentioned earlier, the company hit 200 people, and I moved on. I had gained the experience I needed to get back out and build my next thing, which is what I’ve been doing with Competitive Storytelling now for two years.

Of course I didn’t feel 100 percent equipped, and it was scary to leave the safety of a steady job. Paychecks feel nice but building a legacy requires risk.

If I had stayed, I probably could have learned more. But I also knew it would be an investment of diminishing returns.

The truth is, you’re NEVER going to know EVERYTHING. It’s impossible. Yet we can get bogged down in learning for fear that we’ll make the wrong choice.

Don’t let yourself get paralyzed into thinking you have to collect every piece of information and knowledge before you get started. Dive in and you’ll either sink or swim.

At the end of the day, the life of a founder or entrepreneur is filled with many phases and is all part of the journey. When you know your big vision, you can take the steps to make it happen.

The path to success isn’t linear. It’s going to be bumpy and there might be dead ends. You may feel the urge to plan every step of the way. But you can’t. Take every step one at a time, always looking at your North Star to guide you. Eventually, you’ll get there.

RESOURCES for Founders and Storytellers

Looking for some inspiration to keep going? Check out this conversation between two legends—Mike Tyson and Eminem—as they discuss how they rose to greatness. They both agree that overnight success isn’t possible, and that all greats must struggle and fail before they break.


I recently read Dan Martell's "Buy Back Your Time". The book is a great way to re-evaluate how we as founders and entrepreneurs tend to be the biggest bottleneck both for our business and the life we want to live.

After reading the book, I hired a personal assistant from Athena.  

No affiliates for either of those suggestions but think they might help many of you out.

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