Competitive Awareness as a Founder

sailing, competitor analysis, competitor awareness

For a while, I’ve been publicizing one of my favorite questions for founders.

“What unique insight (that makes money) do you have that either everyone else is overlooking or underestimating?”

I first mentioned it in my thesis. And, which might provide more context, was quickly followed by my related posts on:

For the most part, founders are pretty cognizant of this X-factor. B-schools train their MBAs to seek their “unfair advantange”. And a vast majority of pitch decks I’ve seen include that stereotypical competitor checklist/features chart. Where the pitching startup has collected all the checkmarks and their competitors have some lackluster permutation of the remaining features.

There’s nothing wrong with that slide in theory. Albeit for the most part, I gloss over that one, just due to its redundancy and the biases I usually find on it. But I’ve seen many a deck where, for the sake of filling up that checklist, founders fill the column with ‘unique’ features that don’t correlate to user experience or revenue. For example, features that only 5% of their users have ever used, with an incredibly low frequency of usage. Or on the more extreme end, their company mascot.

To track what features or product offerings are truly valuable to your business, I recommend using this matrix.

And, I go into more depth (no pun intended) here.

Competitive Awareness > Competitive Analysis

I’m going to shed some nuance to my question in the words of Chetan Puttagunta of Benchmark. He once said on an episode of Harry Stebbings’ The Twenty Minute VC:

“The optimal strategy is to assume that everybody that is competing with you has found some unique insight as to why the market is addressable in their unique approach. And to assume that your competitors are all really smart – that they all know what they’re doing… Why did they pick it this way? And really picking it apart and trying to understand that product strategy is really important.”

So, I have something I need to confess. Another ‘secret’ of mine. There’s a follow-up question. After my initial ‘unique insight’ one, if I suspect the founder(s) have fallen in their own bubble. Not saying that they definitively have if I ask it, but to help me clear my own doubts.

“What are your competitors doing right?”

Or differently phrased, if you were put yourself in their shoes, what is something you now understand, that you, as a founder of [insert their own startup], did not understand?

In asking the combination of these two questions, I usually am able to get a better sense of a founder’s self-awareness, domain expertise, and open-mindedness.

Photo by Ludomił Sawicki on Unsplash


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#unfiltered #12 Spilling the Beans – Sharing Insights

idea maze, spilling the beans, sharing secrets

Yesterday, having read my most recent blog post on social experiments, one of my friends asked me why I decided to finally start the blog. My simple answer was “to make myself obsolete”. The question that inevitably followed was:

“Why?”

Although not incredibly common, I’ve had a very small handful of friends and family ask me similar questions. All of which either directly ask or border “Why share all my secrets?”. Admittedly, all is subjective in this case, as I’m not keen on posting my social security or my social media log-in information on here.

  1. Wouldn’t I be more competitive in this saturated (although I argue otherwise) market if I kept them to myself?
  2. On a startup front, wouldn’t sharing the rationale of others and my own enable founders to “game the system?”

In response to (1), your competitive edge in the 21st century isn’t how many ideas you’ve hoarded, but how many you’ve executed on. And frankly, if we can cooperate to build a better world, why not?

For (2), if founders can “game the system” just by reading my blog, which requires them to have concrete evidence for growth and the questions fellow investors and I pose, well then, it’d be a great example of “faking it till they make it”. My blog merely provides a framework, plus a few stories, to how some of the smartest people around have overcome their obstacles. By the time the system tests them, I hope they’ll conquer the adversity in front of them and have the discipline to push forward.

What’s inside the black box?

I’m extremely happy to share “my” secrets. And I use the term secrets loosely, much like Peter Thiel does in his book Zero to One. In fact, the only reason I have any insight into life is that experienced experts were generous enough to share theirs with me. In other words, none of my insights are truly original. All are borrowed from the best, until I create a version that I resonate with more.

Simply put, if my ‘secrets’ and insights help even just one person out there to live a better life, then I’m a happy camper. My goal is to make the future a better place to live in. Oddly enough, it also happens to be one of the reasons I’m in venture capital. Only by sharing what I believe to be right and morally right am I able to help move the needle, if only by a little bit. As I’ve mentioned before, I’m a huge fan of people going through the idea maze and spending time and effort on insight development. If I can help catalyze those motions in my readers through my blog, then I’ll toast to that.

The Flip Side

However, I should mention there are secrets that I will carry to the grave with me. For instance, outside of the obvious, like SSN and credit card info, ones that…

  • My friends/colleagues tell me in confidence,
  • Cause more harm than good in the world,
  • Cause more harm than good to the people around me,
  • Carry malicious intentions,
  • And/or reveal why I put OJ in my breakfast cereal.

Stay curious!

Photo by Tijana Drndarski on Unsplash


#unfiltered is a series where I share my raw thoughts and unfiltered commentary about anything and everything. It’s not designed to go down smoothly like the best cup of cappuccino you’ve ever had (although here‘s where I found mine), more like the lonely coffee bean still struggling to find its identity (which also may one day find its way into a more thesis-driven blogpost). Who knows? The possibilities are endless.


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