What Finish Line?

How this mindset change can make you legendary

September 12, 2022
min read

Welcome back, founders and storytellers.

Every entrepreneur I've ever met has a hunger inside of them, but the startup world is one of attrition and survival. The ones who win are the ones who stay in the fight, round after round.

They are a bit like Rocky.

"It ain't about how hard you hit. It's about how hard you can get hit and keep moving forward."

This week, I talk about the illusion of the finish line and how focusing too much on it can hamper your chances of going from great to legendary.

Ring the bell...let's do this.

DEEP DIVE: The Never Ending Story

You’ve heard it phrased a hundred ways: the finish line, the light at the end of the tunnel, the sunshine after the storm. They’re all metaphors that signal the end of your long, harrowing journey. What a motivator it can be to know you’ve almost made it!

I have some bad news for you. The finish line is a myth.

At least, it is for people who are the best in the world. It could be music, sports, or business. They're all the same.

You see, the finish line doesn’t exist for the best founders. Every step brings new challenges and tests. If you want to be successful, you have to accept up front that your journey will be less like the tortoise and the hare and more like the bear who went over the mountain. What did the bear see when he got to the top? Another mountain.

Serena Williams conquered the tennis world. There's no doubt she will take that same mindset into the venture capital world. The greats never see a finish line.

Instead let me take a quote from my favorite show The West Wing that came up all the time from President Bartlet.

"What's next?"

Let me tell you a bit more about what I mean.

Infinity Wars

Our entire lives, we’re trained to think about goals in a fixed way. A football player’s goal is to win the Super Bowl. An author’’s goal is to publish a book. A CEO’s goal is to make $100 million.

Except it's not true. When Tom Brady was asked which one of his rings is his favorite, he said this: "my favorite ring is the next one."

Elon Musk didn't stop after Paypal. Or Tesla, Or SpaceX...he just keeps building.

As author Simon Sinek points out in his book, The Infinite Game, business—and life—doesn’t work that way. Sinek writes that he frequently hears business leaders talking about being “the best” and beating their competition, and as a result, they make short-term decisions that ultimately doom them to long-term failure. He argues it’s the same reason the US failed in Vietnam and Afghanistan: the US was fighting to win; the Vietnamese and Afghans fought to SURVIVE.

It’s likewise the case when we’re trying to develop personal habits. In his book, Indistractable: How to Control Your Attention and Choose Your Life, author Nir Eyal writes that most people who set goals like vowing to lose 20 pounds or pledging to run a marathon fail because these kinds of goals add misery to their lives, and we’re biologically programmed to avoid things that cause us pain.

Eyal suggests that instead of thinking about your world in terms of specific goals, you should begin an endless journey. This might sound like “I want to cultivate a love of exercise,” or “I want to learn to enjoy building wealth. “You’ll never complete these journeys, and that’s exactly the point,” Eyal writes.

The Pitfalls of Finish Line Thinking

Remember Vanilla Ice? In 1990, his album, To The Extreme, became the fastest selling hip hop album of all time and his anthem, “Ice Ice Baby” was the first hip hop single to top the Billboard charts. And what about all of his other great songs that followed?

After three years of non-stop touring and a cameo in the Teenage Mutant Ninja Turtles movie, Ice decided to take some time for himself. He pursued his passion of motocross racing and got into the Rastafari movement. By 1994, Ice was hooked on heroin and had to be revived by friends after a suicide attempt.

When thinking about success as a finite finish line, even the most talented get into the mindset that once they reach the summit, they’ll always stay there. As life coach and author Robin Sharma explains in his book The Everyday Hero Manifesto, that is almost NEVER the case.

“So many A-listers reach the apex and … stop running their lives at excellence,” Sharma writes. “With all the fortune, success, and scores of people telling you that you walk on water, the ego gets fed to the point of hubris. Companies forget that the customers are the real bosses. The same can happen with title holders. They fall in love with their win and think that because champagne was poured over their heads on the night of their monumental victory, next year’s championship ring is already on their pinky finger.

“A part of them is attracted to enjoying the fruits of their labor—playing more golf or traveling or accepting the level of performance they’re at. But accepting good enough won’t keep you in the rare air of the grand master.”

Sharma has sold 15 million copies. He's written more than 10 books.

There's always more and thinking some arbitrary goal will make you "happy" isn't how high performers are wired. The sooner you and me accept that, the easier it is to navigate the unquenchable drive.

A Legend Never Stops

What’s the difference between a champion and a legend? For champions, the goal is being the best—working hard so they can beat the people around them. A legend, on the other hand, works to beat themselves.

In 1991, Boston Celtics forward Larry Bird was at the end of his career. He’d amassed three MVP awards, three NBA titles, and 12 trips to the All Star game, but his back was so battered that he had to wear a plastic brace to bed. In Game 4 of the playoff series against the Pacers, Bird jarred his back so badly he couldn’t feel his toes. And in Game 5, he bounced his head off the parquet floor diving for a loose ball.

Bird had nothing to prove. He’d already cemented his place in the hall of fame, yet he played like a rookie with a chip on his shoulder. Despite being told by doctors he was done for the night with a concussion, Bird returned to the court and led his team to beat out the Pacers.

“Once you are labeled ‘the best,’ you want to stay up there, and you can’t do it by loafing around,” Bird said. “If I don’t keep changing, I’m history.”

You see the same type of hunger from legends in all fields. Mike Tyson always wanted the next knockout. Steve Jobs always wanted the next massive successful launch. I watched an interview the other day with Chamath Palihapitiya, the 46-year-old billionaire, and he said even though he’s achieved so much, he wants more.

There’s something deeper that drives these sort of people.

One of my favorite speakers is Matthew McConaughey. Maybe it's that sweet Texas drawl or the iconic "alright, alright, alright."

He gave an iconic speech when he won the best actor award back in 2014 about how he thinks about his hero.

"To my hero, thats who I chase. Now when I was 15 years old, I had a very important person in my life come to me and say 'Who's your hero?' And I said, 'I don't know. I gotta think about that. Give me a couple of weeks.' I come back two weeks later--this person comes up and says 'Who's your hero?' I said, 'I thought about it. You know who it is? It's me in 10 years.'

So I turned 25. Ten years later, that same person comes to me and goes, 'so are you a hero?' And I was like, 'Not even close. No, no, no.' She said 'Why?' I said, "Because my hero's me at 35.' So you see every day, every week, every month, and every year of my life, my hero's always 10 years away. I'm never gonna be my hero. I'm not gonna attain that. I know I'm not, and that's just fine with me because that keeps me with somebody to keep on chasing.'"

Not to get too deep, but here’s a tough truth I want to drop on you: we’re all going to die one day.

I wake up every day and realize how lucky I am to go after my dreams. I may have goals I haven't achieved yet, but I know I get that day to make things happen. To chase greatness. To chase my hero.

But when that inevitable day comes, don’t you want to cross it knowing that you did EVERYTHING you could? That you gave it all and never coasted?

When Kobe was asked why he worked so hard he summed it up perfectly.

"I made a promise to myself from that day, that I was going to work that hard every single day so that when I do retire, I have no regrets."

The journey to greatness never ends.

Glad to be on it together.

RESOURCES for Founders and Storytellers

I’ve mentioned a lot of great thought leaders in this issue that can help you reframe your journey to success, but another interesting character is David Goggins. Goggins is a former Navy SEAL who’s made a career out of helping others master their mindsets. His book, Can’t Hurt Me: Master Your Mind and Defy the Odds is a great one. You should also check out his interview with Joe Rogan here, where he discusses the fact that there are no finish lines in life. (He can be a bit of a caricature but still plenty of valuable lessons)

It’s a strange market right now. Economic output is falling, but the job market is strong. But with uncertainty generating a lot of speculation, it’s important for founders to step back and gain some perspective about the environment.

This article from Smart Business shares some tips on navigating an unpredictable economy.

Tech Crunch reported this week that BS and Wealthfront called off a planned deal to sell the robo-adviser startup to the financial giant for $1.4 billion. Why is this important? It might provide an interesting window into what fintech companies may be worth today—and which might be overvalued.

Next week I'll be releasing episode 1 of my own story. You'll get a raw glimpse into my own life and how I got to the point I am today. The best testimonial I've got for it came from my mother: "Son, this is the best video you've made. I had to show your father." If you want to check out the trailer, here you go.


On my flight from Miami to SF, I watched Top Gun: Maverick. Great storytelling.

Then I re-read The Almanack of Naval Ravikant. Two reminders from that book: learn to build and learn to sell.

To wrap up, a quick thank you to the 1,052 readers. In just 9 weeks, the newsletter broke 1,000 readers and maintains a 59.7% open rate.

Know someone who might enjoy it? Please pass it along!

See you next week.

Looking for personalized help with your storytelling or fundraising? If you're a venture backed founder, I coach a select few founders that are building unicorn startups. You can reply to this email for more details or apply at the Founder Fundraising Program.

If you're curious the types of founders we work with, here is what the co-founder and Chief Medical Officer of Levels, Casey Means had to say about working together:

"Robbie's Performative Speaking program facilitates effectively communicating our vision with my company Levels. I'm trying to start a global movement around metabolic health and real time biofeedback on diet and lifestyle. My mission is to reverse the chronic metabolic health epidemic for me to be successful in this mission.

It requires that I inspire and empower others with the vision that is in my heart. And in my mind, whether that's investors, the healthcare community, potential members, advisors, or professional partner. I am extremely grateful to Robbie and the team for giving me the tools to up level my voice and my effectiveness to tap into narrative in my communication and my speaking, and to learn to connect through my speaking."

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