The 'Good Enough' Trap

Why complacency is holding you back

October 3, 2022
min read

Welcome Back!

As I'm wrapping up my trip to Amsterdam and then Spain, I'm reminded...

there's nothing more powerful than a world-class storyteller.

On Thursday this week I watched as one of the founders I coach, Victoire Cogevina Reynal, stood on the main stage at the World Football Summit and told the story of how she built her startup Gloria to bring gender equality to the sport of football.

That story ended with the news that the German Unicorn company, One Football, had acquired her startup and was elevating her to the role of VP for Women's Football inside of their powerhouse company.

Victoire is a world-class founder and she never settles for just being good.

Let's talk about that some more this week.

DEEP DIVE: Good isn't Good Enough

Good storytelling founders are the ones who suffer the most.

That’s not something you’d expect me to say, right? Let me explain.

When it comes to storytelling, I’ve found there are three tiers of proficiency: mediocre, good, and great.  The vast majority of founders I talk to are in the good category; some are mediocre. Only a handful—3 to 5 percent—are truly great.

There are a small number who can reach a 4th tier that is world-class. Think the top 1% who have natural ability and then an obsession to reach the top.

If you think about it, that classic bell-curve distribution translates into just about every area of our lives. Rappers like Lil Wayne or Coolio (RIP) are good and made successful careers for themselves, but can you tell me with sincerity that they’re ICONIC? Not when compared to the likes of Jay-Z, Tupac, or Eminem.

The same can be said of professional athletes. A high school football player has a 0.00075 percent chance of making it to the NFL, but the chances of becoming the next Jerry Rice or Tom Brady are even slimmer. All NFL players are good—only a handful are GREAT.

But Robbie, you think, plenty of people are good and still successful. Isn’t good sometimes good enough?

Here’s why that line of thinking is dangerous—and what you can do about it.

Complacency Kills

Our brain comes up with all sorts of wacky ways to preserve our sanity. We’re born with an immense set of cognitive biases, each of which color the way we think about the world and ourselves.

One such bias is called the Dunning-Kruger effect, a theory that causes us to overestimate our competence or knowledge in a given domain. Put simply, we think we’re better than we are at most things. I see this bias in action when I work with clients. Each believes they’re in the top 20 percent of storytelling founders—which is statistically impossible.

What’s more: studies have shown that the lower your competency, the more overconfident you become. “If you are incompetent, you can’t know you’re incompetent,” David Dunning wrote in his book, Self Insight. This explains why it’s hard for you to ask for help when you’re learning a new job or skill—you don’t know what you don’t know.

This tendency often becomes a problem because it gives you a false sense of expertise or mastery. You think you’re a good storyteller, so you get complacent and stop working on your craft.

Many tragedies have come as the result of complacency, such as the 2010 Deepwater Horizon explosion that killed 11 people and caused a massive oil spill that took months to clean up. Some historians even theorize that complacency—not hubris—was the root cause of Ancient Rome’s collapse.

Of course, you being a good-not-great storyteller probably won’t topple any empires, but there’s a good chance it will make your fundraising rounds long and stressful.

You’ll meet with investors and hear the same old thing: “we like the story and would love to stay updated.” Translation: they like you, but they don’t feel the FOMO. Your pitch and story are good, not great.

To put it another way, think about eating at a good restaurant. You like it, would recommend it if someone asked, and you’d go back again. But a GREAT restaurant? It’s the first thing you talk about for the next week.

From Good To Great

So how do you make that jump from good to great? There are no guarantees, but it starts with acknowledging—and accepting—the fact that you’re probably not as good as you think you are.

“Complacency is the last hurdle standing between any team and its potential greatness,” NBA coaching legend Pat Riley once said, and he’s absolutely right.

Once you’re aware of that tendency in yourself, you must work on your craft every day, and you must do it relentlessly. Let’s stick with basketball for a minute. What’s the difference between Allen Iverson and Kobe Bryant?

Both were drafted in 1996—Iverson went to the Sixers with the 1st overall pick, and Kobe to the Hornets with the 13th. That year, Iverson won Rookie of the Year, averaging 22 points per game. Kobe averaged just 7.6. The AI/MJ comparisons were rampant.

Fast forward a few years. Kobe collected five championship rings. Iverson? Zero. Kobe will go down as a Top 10 all-time player. AI ended his career in Turkey.

Now don't get me wrong, AI is one of my favorite players because of his mindset on the court. He was fearless. But even he talks about Kobe in a completely different way than himself.

Why did these careers diverge so wildly? My not-so-hot take is that Iverson was unwilling to refine his natural skills. He refused to spend time in the weight room, and famously questioned the importance of practice. In other words, he got complacent.

Kobe, on the other hand, was the first player in and the last player out. “I heard the ball bouncing. No lights were on. Practice was at about 11, and it was 9:30,” former Lakers player and coach Byron Scott said. “And I go out there and look, and there’s Kobe Bryant. He’s out there shooting in the dark. And I stood there for probably about 10 seconds, and I said, ‘this kid is gonna be great.’”

That’s what greatness looks like. It’s the hours in the dark when no one’s looking. Bryant knew he was one of the greatest, but he never stopped working on getting better.

That’s what it takes if you want to jump the fence from good to great.

The Journey to Greatness

By now you might be saying to yourself, I get what you're saying Robbie but tell me the how to do it.

I always hated watching those webinar videos where they would never tell you the how and then make you book a call. They always said it's a free deep dive with no pressure and then it turned into a 100% pressure sales call.

So here's what I've learned in my own journey.

Back in my early law days, I tried a driving while intoxicated case. It was my 8th jury trial in my career and I was puffing out my chest telling my office how I was going to finally beat this defense attorney who nobody could seem to take down.

I had a strong case with great facts. No doubt about guilt.

Then I lost.

The jury told the defendant this after the case: "We know you were guilty. You know you were guilty. But we believed you when you told us your story about being sorry and doing better in the future."

They then told me that I had done a "good job". Good job. I never want to hear those words again.

That day changed everything.

So here's what I did to make sure I never heard those words again.

First, I found the best speakers and storytellers in the Dallas legal community. If I wasn't in a court trying a case, I was watching them. I'd sit and watch hours of their trials and then stay super late to get my work done.

I built relationships with them and would sit in their offices listening to how they prepared and became a sounding board for their storytelling. That helped me pick up on things they did deliberately and things they did instinctively. My goal was to provide them meaningful help in preparing and also absorbing the best strategies and tactics they used.

Next, I opened up books, google, and youtube to learn as much as I could. The mistake people make when it comes to storytelling is thinking that it's just about studying storytelling.

It's not.

I studied brain science and persuasion. I looked at copywriting and advertisements. I spoke with psychologists and scientists. I analyzed politicians and they way they spoke in public and on television. I watched the way the best screenwriters created emotional moments in movies and television.

I read fiction. Lots of sci-fi and fantasy and thrillers. I wanted to learn how to build worlds and keep people captivated to keep turning the page.

After that, I was relentless in getting feedback. After every single jury trial I would walk back to the jury room, win or lose, and ask them a simple question.

"Be brutally honest with me, what did you like but more importantly what didn't you like that I can improve?"

Let me tell you, they were brutally honest. Most of my colleagues only wanted to hear the good.

I wanted the bad.

They'd stay and talk to me for hours after the trial. Even though I'd be exhausted from a week long trial, I'd stay until 7 or 8 pm listening to the jury give me the feedback.

The last piece of this is I never thought I was good enough. I still don't.

There's always room to improve.

This past year I've spent a bunch of time working with a voice coach to go deeper and improve my ability to control tone, timbre, and turn it into a full on instrument.

I've worked with copywriters this year too to look at my videos and break down how those stories come across. Where could I tighten things up, where could I create a deeper emotional hook, where can I improve.

For the keynote I delivered in Amsterdam last week, I worked with one of my good friends, mentors, and a highly paid professional speaker to refine that talk and make sure I would create the right memorable and portable moments.

Greatness doesn't happen overnight.

Greatness doesn't happen alone.

I'm still on my quest to reach that pinnacle.

What's stopping you from starting yours?

RESOURCES for Founders and Storytellers

Since our country’s founding, one of our core values has been that of innovation. In many ways, the risk-taking and relentless pursuit of better has brought the US to the forefront of technological and industrial advancement. But some economists argue that time has passed, and we are now in a period of complacency that threatens our standing in the world. This presentation by George Mason University economy professor Tyler Cowen explores his views on the dangers of the “good enough” mentality.

Down rounds often signal risks of a struggling business to future investors. But according to a new PitchBook report, contrary to expectations, venture-backed companies that have taken on a down round are likely to continue on the path to growth—including raising new rounds and restructuring following a buyout.

How can founders best prepare for riding out the potential lean times ahead? This Q&A with Insight Partners VC managing director Hilary Gosher discusses how founders can cut out what she calls the “fluff in the system,” as well as how to approach layoffs, extend runways, and reprice employee stock options.


You might have seen the recent announcement that I joined Antler as a Venture Partner. It's exciting to have this opportunity as well as my partnership with 776 to continue helping more founders that are backed by amazing investors.

I'm still building Performative Speaking and coaching world-class founders. We just crossed $315,000,000 raised by the founders I've coached. The craziest part is that this number could break 400 million by end of the year. I'm so damn proud of all the founders I coach and the companies they are building.

There are more big announcements coming over the next few months. So stay tuned!

See you next week.

There's currently a waitlist to work with us. If you're looking to fundraise in Q1 or Q2, you can apply to claim a spot on the march to 1 billion dollars raised by founders we work with by going here.

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