Building while Flying

All Things Venture #010

Hey Everyone - Dez here from Apex. When I was ten, I had an absolute banger of a birthday party. Let me set the scene for you. It was me, 12 of my closest 5th grade buddies, and my mom took us all to the Chili’s in my neighborhood. Now obviously Chili’s isn’t the pinnacle of fine dining, but in suburban Texas circa 2004, to a newly minted ten year old? It might as well have been Eleven Madison Park. I thought I was OG Jim Jones, Ballin and so did my friends, so naturally we all ordered cheeseburgers, fries, and drank as much soda as humanly possible. From there our caffeine riddled bodies went back home, ran around my house, pissed off my sister, and let her guinea pig out. My entree in to young adolescence could not have been more glorious. Ever since then I’ve loved celebrating birthdays, and while writing my tenth article for All Things Venture is certainly not a birthday - it is a milestone, and it’s worth reflecting on. Personally, I hate articles or videos that start with “10 THINGS I LEARNED ABOUT X” or “6 EASY STEPS TO Y”, so I won’t bombard you all with easily googlable information. So in the spirit of reflection (and reliving my tenth birthday party) here goes nothing.

One phrase I hear related to startups a lot is this whole concept of, “we’re building the plane while it’s flying.”

On first brush, that statement is absolutely insane. Who in their good god damn right mind, would ever take that unnecessary of a risk when there are plenty of other options of transportation available? Well. The answer is simple. Entrepreneurs take that risk. Entrepreneurs relish in that risk. Entrepreneurs absolutely love that risk. And as someone who has sat in the seat of an entrepreneur, I fully agree with the statement. Building a startup is like building a plane while it’s flying. However, just because you’re 30,000 feet in the air, that doesn’t mean you can’t have a map, or a guide. One benefit I get from running All Things Venture, is that I get to speak to all the pilots of these in-progress-planes, and I get to hear how their problems overlap. So because I’m feeling so #reflective, I’ll share them with you. But also because I hate those “10 THINGS I LEARNED ABOUT X” or “6 EASY STEPS TO Y” articles, I’ll try to switch it up a little bit:

Alright, so the general components of any normal flight are that you’ve got your passengers, you’ve got your crew, and you’ve got the plane. The plane is your startup. This is your baby. It’s a hunk of metal hurtling through the sky seeking it’s destination and that destination is being able to ring the bell at the New York Stock Exchange like ten years from now, while “We Made It” plays in the background and everyone reminisces on the fact that SOULJA BOY WAS A FEATURE ON A DRAKE SONG (Don’t worry, I forgot about it too here’s the link). So, we’ll circle back to the plane, but let’s talk about those passengers. If building a company in general is like building a plane while it’s flying, then attracting early users is like selling tickets in first class while coach is being built. Those early users are going to, in my opinion, make or break the business, so if you do anything when you’re first starting your company do this - speak to customer’s early and often. I cannot stress this enough. If your first class passengers tell you they prefer to have White Claw as their alcoholic beverage of choice don’t waltz over and let them pick between Bud Light and a $12 Pinot Noir. You have sold your passengers the dream of first class, so live up to it. Don’t bring them Bud Light. Bring them White Claw.

Continuing on with the building while flying analogy, your crew is an equally important piece of the flight. The way I see it, it’s kind of like this. The CEO is obviously the Pilot. The Co-Pilot can be any combination of members on the executive team (Think CFO, Head of Product, Head of Engineering, CMO, etc.), and the “do-ers” in the company, which is essentially anyone who isn’t the Pilot or Co-Pilot, are the flight attendants. One thing about building while flying, is that you’re all in it together. Everyone’s job, no matter if you’re leading the front end UI development of a new sign up flow, or managing charge backs to protect against fraud in your checkout, is important. The Pilot will undoubtedly set the direction, but the Co-Pilot and the flight attendants are the people who ensure you’re going to have a smooth flight. There’s always a balance between direction setting and doing depending on how mature the startup is, but generally the later stage the startup, it will be more direction setting and less doing for your Pilot and Co-Pilot(s). So why does any of this matter? Well remember, your plane is half built right now, and you have customers in first class who expect White Claw. Your Pilot needs to focus on the flight path, and your Co-Pilot needs to focus on helping them land the plane. So that means that, through hell or high water, your flight attendants need to deliver those White Claws; and they need to deliver those White Claws while coach is still being built, your plane is 30,000 feet in the air, and you’re probably going through turbulence. All of this is really meant to say is that when you’re building your crew, you’re building culture. You’ll need to have a team that communicates well, trusts in one another, and can navigate massive amounts of ambiguity.

Last but not least, is the plane itself. Let’s set the stage. You’ve built your crew, you’ve attracted your first passengers, and now you need to get them on the plane and on their way. Is the plane built for speed? Or for comfort? Is it designed for convenience? Or for luxury? Is it headed to a tropical getaway? Or a winter retreat? There’s a nearly infinite set of decisions to make and each decision can pull you closer to the sweet, sweet promise land of the public markets OR send you hurtling to the doom of a TechCrunch article announcing the dissolution of your company. Either way, what I think is the most important thing to understand about startups, and building while flying, is that few of those early decisions you make are final. The beauty of building while flying is that few things are permanent and you can chuck all of your bad decisions out of the exit windows to help stabilize the plane. By all means, it’s much better to get it right the first time, but if you’re wrong, which you inevitably will be, don’t agonize over your past decisions, cut bait, bring in the new seats, get the fresh paint job, buy the 10% ABV White Claws (That’d be crazy if they actually existed right???), and go at it again. You’ll need luck, you’ll need resilience, and you’ll need to adapt, but there are honestly few work experiences as thrilling, or as unique as building while flying.

That’s it for this week everyone - hope you all enjoyed the article and don’t forget to subscribe!

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