Why So Serious?

Being a founder is hard work—but that doesn't mean you can't have fun

September 26, 2022
min read

Hello from Amsterdam,

Today we've got the lucky 13th issue of The Storyteller’s Playbook. When I started writing this newsletter, I literally had zero subscribers. Since then, 1,121 of you have signed up for tips and inspiration on becoming a better storyteller and founder. The best part...we're just getting started.

It's been an amazing week. I traveled to Amsterdam to deliver a keynote address in front of a group of European venture studios and VCs.

The 30 minute keynote discussed why the startup ecosystem should be backing the ambitious and hard ideas. We need this generation's version of JFK rallying 400,000 people to put the first man on the moon.

This week two of my coachees (h/t Matt Mochary for the term) closed their fundraising rounds!

One closed their seed and the other closed his series c. Just goes to show, even in the toughest fundraising environment, great founders still get funded.

Now let's dive in.

— Robbie

DEEP DIVE: Founders Just Wanna Have Fun

I never smiled in pictures for the first two years after I founded my business.

If you know me or have seen any of my content, you understand how ridiculous that is. Most of my life, I’ve been a happy person, smiling my way through the toughest times. But I worried that smiling too much made me come off as goofy or unprofessional.

There’s a great scene in the Christmas movie Elf where Will Ferrell tells grumbly department store manager Faizon Love that smiling is his favorite. Love frowns and says, “Make work your favorite. That’s your favorite now.”

That’s exactly how I felt when I started my entrepreneurial journey. In order to be taken seriously by investors and potential clients, I had to show everyone how serious I was about the work.

See what I mean?

I look back at this and laugh. Ridiculous in so many ways.

But after a while, I realized how tiring it was to purport myself as this stoic, capital-b Businessman.

It also dawned on me that I wasn’t practicing what I preached. I tell my coachees all the time to be themselves and let passion shine in meetings and presentations. My work is my obsession and it fires me up—why shouldn’t I let the world see that?

Once I became attuned to this tendency in myself, I began noticing it in other founders as well. These people who were the life of the party in social situations were suddenly so dry and dispassionate in their investor meetings and all hands calls that they blended in with the beige walls.

Yes, it’s important to build your ethos and convey calm and confidence in the face of adversity, but nobody said you have to become Ben Stein.

These days I think about it more like Leonidas in 300. Calm in the face of chaos but always bringing his personality and charisma to inspire his troops.

Another recommendation comes from Aaron Burr’s advice in Hamilton: talk less, smile more. But if you’re still having trouble finding your fun groove, here are some tips to get there:

Shift Your Mindset

Part of the reason you might feel so serious is because, well, starting a business is freaking HARD. You already know that you’ve got a long journey ahead before you see the fruits of your labor, and you feel like having too much fun will somehow invalidate your product.

It’s not totally your fault.

Our brains are wired for survival, which means that we’re constantly scanning our environment for threats and things that can go wrong. This was a very useful trait when we were living in caves and avoiding saber-toothed tigers, but in the modern world, it means we tend to focus on the negative far more than we do the things that are going well.

I encourage you to fight against your biology and reframe your perspective. Remind yourself that you are EXACTLY where you want to be right now. How cool is it that you get to live your dream of building your own company?

This is something I did when I was freezing my butt off during 15-degree baseball practices. It was easy to be in a bad mood, but by stepping back and gaining some perspective, I realized that I was exactly where I wanted to be—playing the sport I loved.

Now that didn't mean that I loved those early morning practices when I couldn't feel my hands, but I knew that this was part of the deal.

Without those miserable practices (and for a Texas boy, those temperatures were miserable), I wouldn't have been ready on game day to do the one thing I loved most. Win.

I’m sure you’ve heard the old chestnut “it’s the journey, not the destination,” right? If you spend your whole time thinking about achieving your goal, you’re missing out on all the great stuff that’s happening along the way. It’s like Ferris Bueller said: “Life moves pretty fast. If you don’t stop and look around once in awhile, you might miss it.” (Did I just make TWO Bueller references in the same newsletter? I sure did.)

Let's add one thing here that I see mess up too many founders. You can't ONLY focus on the journey. Too many founders love the journey but don't have any idea of where they want to end up. That just creates a meandering journey with no big payoff for all the hard work.

Know the end goal AND enjoy the journey.

Gamify Your Gains

Here’s the reality of any job: it’s going to suck about 30 percent of the time. We all get bogged down in the drudgery of our work lives from time to time, but it doesn’t have to be that way. Instead, find the fun in the tedium.

In his book, Indistractable: How to Control Your Attention and Choose Your Life, author Nir Eyal suggests you can find novelty in just about any task. “The great thinkers and tinkerers of history made their discoveries because they were obsessed with the intoxicating draw of discovery, the mystery that pulls us in because we want to know more,” Eyal writes. “Whether it’s uncertainty about our ability to do a task better or faster than last time or coming back to question the unknown day after day, the quest to solve these challenges is what can turn the discomfort we seek to escape into an activity we embrace.”

What We Appreciate, Appreciates

I first heard that idea of "what we appreciate, appreciates" from my close friend and fellow founder Alejandro Navia.

Which brings me to the final tip.

I encourage you to start incorporating this idea into your life right away to feel more gratitude. As I said above, we often focus on the hard, negative things and forget about all the wonderful things we have going for us. One way to change this tendency is to practice being grateful.

Gratitude has long been lauded by the world’s premier spiritual experts as the secret to not only living a healthy and happy life, but making your wildest dreams come true. It’s a cornerstone concept of the Law of Attraction, the idea that whatever energy you put out into the universe is what you will get in return.

It’s the principle at the foundation of Think And Grow Rich, the highest-selling self-help book of all time, as well as Rhonda Byrne’s The Secret, which became a blockbuster bestseller in the early 2000s.

But even if the Law of Attraction stuff is too woo-woo for you, science backs up the importance of gratitude as well. A UC Berkeley white paper shares that numerous studies support the idea that people who practice gratitude have better physical and psychological health, increased happiness and satisfaction, and decreased materialism. In short, they have more fun.

I don’t know if I buy everything the spiritual gurus preach, but this one works.

Spend some time each day thinking about the great stuff you have going on. It could be your family or your career, or it could be a sunrise or a good meal. Whatever your brand of happiness, the more you appreciate things around you, the more fun you’ll have.

The brain is a muscle. Just like going to the gym with frequency will get you gains, practicing gratitude on a regular schedule will actually rewire the way your neurons fire. You’ll notice the great things in your life with more frequency, and as a result, be happier and more satisfied.

Don’t get caught up in taking yourself too seriously. If you’re constantly delaying your own gratification thinking the prize is coming at the end of the race, you’re sadly mistaken.

Have fun along the way.

Watch the wins pile up.

RESOURCES for Founders and Storytellers

Earlier, I mentioned Nir Eyal’s book, Indistractable, and it’s such a great resource I think it bears repeating. Nir spent several years studying why we get distracted and how we can become more productive with our days. If you’re the type of person who finds themselves scrolling through Instagram when you should be working on that big proposal, this book’s for you.


While I’m on the Ferris Bueller kick, I definitely recommend you watch Don’t You Forget About Me: A Tribute To John Hughes. Hughes is the legendary writer and director of the most iconic films in the ‘80s—including Sixteen Candles, Home Alone, and National Lampoon’s Vacation—and this documentary digs into his storytelling brilliance as well as his disappearance from the limelight leading up to his death in 2009. BONUS: Re-watch Ferris Bueller’s Day Off, which is currently on Netflix. Its theme is a nice reminder that you shouldn’t take life so seriously all the time.


The overturning of Roe v. Wade sent a huge shockwave through the country, and while the nation recovers slowly, the venture community is already beginning to act. This TechCrunch article shares thoughts from eight investors about the toppling of Roe, its impact on the venture community, and what they think about activism via investing.


I saw a trailer for the new Netflix documentary on The Redeem Team. It chronicles the 2008 US Men's Basketball team in their quest to regain the gold medal at the Beijing Olympics.

Let's just say that Kobe Bryant was built different and his competitiveness is something to be admired. You can check out the trailer here.

If you believe this newsletter can help other founders and storytellers, would you share it with them?

See you next week,



If you're looking for more help to raise $5m or more, you can check out The Founder Fundraising Program. Join the waitlist there to work together when spots open.

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