What the TV show Louie can teach us about start-ups
Achieving greatness means looking like a fool.
As I watched an episode of Louie this Sunday morning, I couldn’t help but think of my experience starting a company. If you’re not familiar with the show, Louie plays a comedian on the brink of greatness or complete failure; a spot I suspect many entrepreneurs have found themselves in.
The big opportunity
Louie has the chance to take over the Late Show from Letterman, and Jack Dall (pictured above) is assigned by CBS to get him ready for the audition of his life. It’s soon clear Jack’s real job is to serve as a catalyst for Louie to face the basic question facing anyone on the brink of something great: Are you willing to go all out for it? To risk looking like a fool if you don’t get it? Because if you aren’t, it doesn’t matter what else you do. You’ll come up short. You may not fail, but you won’t be great.
In the opening scene of the episode, Louie is seated in Jack’s office, and Jack tells Louie to make him laugh, on the spot, no questions asked. But Louie resists.
That’s when Jack says:
Well here’s the thing with that champ — that’s short for champion. If you want to be a talk show host, it’s better if you’re funny. Let’s see it: Let’s see the funny. Make me laugh! Go!…3..2..1..Go!
Louie stumbles. He looks at Jack uncomfortably. He makes excuses:
I’m not that kind of funny….The kind where you just say go and I’m funny. There’s different kinds of funny. There’s different kinds of performers…
But Jack knows the industry fundamentals:
Let me tell you what kind of what you are: You’re whatever you have to be to make people laugh. Anytime. Anywhere. Anyone! You turn it on on a dime. You get that belly moving son or you’re out.
Jack lays into him:
Now tell the truth, you’re scared, like a rookie. You’re like some kid at a talent show with a number pinned to your shirt. You got nothing, or you would have shown [it] to me now. So get out, thank you, have a nice day.
There’s nothing worse than the moment you seriously consider that you might just be faking it. And it’s in that moment, as Jack is kicking him out of the office, Louie finds his reason for being willing to look like a fool. To really go for it. He has nothing to lose.
Look, I can’t give up on this. I don’t, ah, this is either a door or a wall for me; it’s either the beginning or the end.
But Louie still can’t think of anything funny. So he does the only thing he can think of to show him he’s willing to go all out: He starts dancing like a ballerina, waving his hands and calling Jack a “pencil penis.” It’s not funny. He looks like a fool. But a fool who is trying.
At the end of the episode, Louie is in his dressing room about to go out to do his big test show — his pitch to network executives for why they should pick him to take over for Letterman. It’s the moment Jack prepared him for. Jack gives Louie some words of advice we can all take to heart; the words of any good mentor who isn’t bullshitting you:
I’ve told you what I know, and the rest is up to you. It’s just, if you can do it. That’s it. Listen, you’re a good guy. I’m not going to say ‘I think you can do it’ because I really have no idea. But I hope you do.
And now I’m going to tell you what I know to be the three rules of show business.
Number one, look them in the eye, and speak from the heart.
Number two, you gotta go away to come back.
And number three, if someone asks you to keep a secret, their secret is a lie.
Jack summarized the big lessons I’ve learned while running a start-up for over 2.5 years
(1) Just like success in show business, success in entrepreneurship is notoriously difficult to predict.
No one knows if you can do it. You either do it or you don’t do it. The middle ground is failure. You can listen to people’s opinions, but the smart money is on them being wrong.
(2) Don’t kid yourself about how you’re doing.
Making excuses for not having users or paying customers is the same as a late night talk show host making excuses for why he’s not funny.
At H.Engage, I kept making excuses for our inconsistent average number of daily users and monthly recurring revenue, which were spiking up and down. I said “we weren’t that kind of start-up.” We were selling to big companies that were only using our product for a few weeks at a time.
That could have been OK, if I wasn’t trying to build an enterprise SaaS business, the fundamentals of which are based on growing monthly recurring revenue and users. Once I looked past my excuses, I came to terms with the fact that I had a serious business model problem in need of fixing. We had to change the product and value proposition. I had to admit that while I was successful at selling and generating revenue, I was failing at building the type of business model I wanted. That was a catalyst for us to make some scary changes, but ones that have paid off big.
(3) Don’t be afraid to look like a fool.
Looking like a fool is the path to greatness. You have to be willing to put yourself out there for people to judge. I spent over two years unable to clearly explain what H.Engage did. Instead of talking to people about it and putting my ideas out there for criticism to help refine them, I hid away and tried to figure it out behind a closed door on a whiteboard.
The reality is that you figure things out by talking to customers, investors and others. Often, these interactions will raise questions you can’t answer, and inevitably you will feel like a fool. But don’t be afraid of those moments. Embrace them, learn to love them. It’s when you’ll learn the most. I knew I was on the right track when I could finally explain H.Engage in a sentence people intuitively understood:
We’re reinventing the bulletin board by making it easy to create and post engaging communications for any organization.
Hate it? Love it? Think I’m missing something? Tell me why, I’d love to hear from you.
(4) Look them in the eye.
It could be a customer or investor, but either way don’t let anything — their lack of attention, the circumstance of the meeting, whatever — deter you from speaking from the heart, from fully engaging. There will always be no’s. But lack of conviction shouldn’t be why you get a single one.
I recently met with a VC who said he was between meetings and didn’t have much time to chat. I’m not sure I’ve ever met with a VC who didn’t say that to me. And in those moments, you have to disregard that statement. You have to make a tired person who is drowning in work believe that this 30 minutes is more important than they thought it was. That life will shift in those 30 minutes and they will see something new. If you can’t come to those meetings with that sort of conviction, don’t come at all.
(5) There will always be forces to deter you.
They’ll make you want to quit. People. Companies. Press. If start-ups were easy, someone else but you would be doing them. Recognize the barrier. Don’t dismiss it, simply categorize it as another piece of data to keep track of. Another piece of external feedback.
(6) No matter what, continue to execute.
Because execution is what separates people that look like fools from actual fools. Embracing the Lean Start-up and your ability to pivot is no excuse for constantly changing to a new direction without fully executing your last one.
For example, at H.Engage, we nearly mistook a lead generation experiment as a success when it was really a flop. Kate on our team was tasked with manually finding HR people on Twitter and then reaching out to them. One of the first people she reached out to replied — we were ecstatic. If this was a repeatable strategy, we could hire inside sales people to do this kind of outreach. But Kate didn’t stop. It was monotonous, manual work. She kept going with the experiment and reached out to 39 more people. Not one replied. We ended up with a 2.5% response rate. That helped establish a baseline to benchmark the cost of an inside sales person for lead generation versus using native ads. Instead of spending 20 hours of Kate’s time to get one lead ($650) we could spend $2.50 per click on a Twitter native ad, and as long as 1 out of 100 people went on to sign-up for H.Engage, we were saving 60% relative to Kate doing it. That has serious implications on our staffing model. If not for Kate executing all the way through, we might have set ourselves up for a very nasty surprise.
The distance between a plan’s success or failure can be short. Don’t use a shiny new object as an excuse to avoid work that you’ve been putting off, just because you don’t want to do it. You have to follow through and finish the swing before thinking about the next pitch.
Get yourself a Jack
There’s nothing I’ve experienced quite as lonely as being an entrepreneur. What I’ve learned is that though you may be facing a unique set of challenges, the building blocks of those challenges have been seen by the Jacks of the world, and they’re ready to help. My Jacks have been Geoff Hyatt, Michael Cho and Dale Larson. Three people that have never been afraid to tell me I’m full of it one moment, and deliver a life lesson the next. We all need a little help achieving greatness. And maybe that’s the main lesson here.
This post was written about Louie, Season 3, Episode 12, “Late Show, Part 3." You can watch it on Netflix or Amazon Prime.
