Podcast: The most important question founders should ask themselves

Podcast: The most important question founders should ask themselves

Founders tend to question themselves A LOT. However, there is one question that is perhaps the most important to ask yourself both at the start of building a new company and even when you find yourself in the middle of one. What is that question? Listen to find out. 

Listen to the Podcast:

Rough transcript:

(Not copy edited)

Hello and welcome all the new listeners who subscribed recently. This is a short solo podcast where I rant about various startup things while also trying to provide help for early-stage startups. I release new episodes every week, roughly. Of course, once I announced this podcast, I immediately started traveling and got jetlagged and then sick. So I’m recording this from the road, without a proper mic, and with a stuffy nose. Apologies if the quality is not so great on this one. But as they say, the show must go on, and this week’s topic is relevant to my jetlagged and sleep-deprived brain as the topic is dreams. Or more specifically, building one’s dreams. Let’s jump right in. 

Perhaps it is safe to say that investors ask a lot of silly questions during a pitch meeting, but there was one investor question that always stuck with me as being more profound than the rest. The question was, “Why do you want to do this for the next 10 years of your life?”. I am hopefully remembering and attributing this question correctly to Hunter Walk, a Silicon Valley investor and former exec at YouTube. I love this question so let’s break down what it means for founders as you ponder your own answer. 

To start, it’s a really good question because it can smack a founder right in the face with the reality of just how long it takes to build a really big business. As they say, the secret to overnight success is that it just takes many, many years. A decade is perhaps a safe average when it comes to trying to estimate how long it will take a founder to launch, scale, and hopefully exit their business. Even super well-funded startups like Uber or Airbnb took this long to get to the public markets. I’ll take a wild guess and say that you probably don’t have access to the same billions of venture capital that they did, so it might even take you a little bit longer.  

While you’re thinking about how to answer that question, let me give you a little more fodder to aid your contemplation. That actually takes the form of another related question to this one and serves as a good starting point. That question is, “are you building your own dreams, or someone else’s?”. Or said differently, are you building something due to an intense personal passion, or are you simply chasing the latest trends in our industry? If the latter, it might be much harder to answer that initial 10-year question because who knows if today’s trend will be around in 10 years, let alone 24 hours. 

A great recent example of this is the hype and commotion around web3. Now, I would love to rant about how so much of web3 is just weaponized Ponzi schemes or that they have no real practical applications; however, someone whose opinion I really value, said I should try to keep my podcasts rants a bit less pessimistic. They are probably right, and besides, taking a swing at crypto or meta whatever these days is just too easy, even for me.

However, I still want to poke at this subject a little today. As I see so many former web2 guys and gals who are now today’s web3 experts and megaphones. Funny how that happens… but I worry a little bit for them as it is certainly a risk to pivot oneself completely around the buzzwords of today. I mean, I wouldn’t do it, and I make plenty of reckless life decisions. Although you know what, I can relate, as someone who built a subscription commerce company at the very peak of that trend many years back. That being said, and from my experience, you don’t want to be holding the bag, to use crypto slang, when an industry trend ultimately collapses. Of course, I could be wrong about a lot of things, so maybe your decentralized metaverse-based Dracula coin NFT  is going to change the world, I mean who’s to say really? Maybe it doesn’t matter if you personally have so much passion for that new shiny trend that you are more than ready to put a decade into figuring out how to make these dreams a big business. In these cases I can only salute you for both your conviction and your stubbornness. These are after all some of the best traits a founder can have. 

For everyone else still building your web2 or maybe even web4 dreams, let’s get back to that question at hand. “Why do you want to do this for the next 10 years of your life?” Is your answer to this question already clear? If it is then great! If not, and to help you further, I’ll share two types of good replies I’ve heard over the years. 

To start things off with a mic drop, one way to respond to such a question could be, “I was just so unhappy with the way this was done, I had to build a better way.” These founders get it as they are quote mission-driven unquote, and absolutely obsessed with their solution. An example of this might be the founder of Zoom, who couldn’t build what he wanted while employed at Cisco. So he left and did it all on his own and in a super crowded market as well. There was a million reasons why that would not work but his passion to build his solution superseded all those reasons. If you’re nodding and thinking this is you then be sure to mention this in your investor meetings with all the confidence you can muster. Show them that extreme unhappiness and desire to do it better, all the while you regal them with stories of how you’re turning your own dreams into a reality. 

Another good response to this question is your ability to articulate how you know something that your industry or competitors simply don’t. This one is a bit tougher to pull off. It is worth mentioning that investors also love to learn things in pitch meetings, even if they sometimes act like they already know everything. If you can teach them something new *and* really unique, you might find them generally more interested and engaged. Related to this, I often tell founders investors don’t want to fund you to learn something, such as how to get product market fit or to validate a growth channel. This is often expensive and uncertain. It is always better to go to them and show them what you have already learned and how with their money, along with those learnings, you know what to do. They probably also want to see what you have learned is big and interesting enough to keep you more than busy for 10-plus years. 

I know these example replies are a bit broad but hopefully helpful to get your own train of thoughts going. Every business is of course different, so really, there are so many different ways to answer that 10 year question. You could maybe argue there is no right or wrong way answer. In the end it will come down how you answer it, either to yourself, or to an investor, and if at least one of those parties believes you. Hopefully, both do! Either way, I might recommend thinking more about this question tonight. And if there’s no clear and believable answer, well, maybe there’s something else to think about. You might not be building the right business if you can’t scan ahead a decade and see yourself working on the same challenge.

Until next time, sweet dreams, founders.