Lesson #3: more miscellaneous lessons
getting stuck in limbo; countering your innate bias; ruthless depth-first search; and being pushy; people like entrepreneurs
Coincidentally exactly a month after my previous post, I started feeling the urge to jot down some more lessons learned along the startup journey. Maybe there’s a natural cadence to these sorts of things, like one of those water park buckets that slowly gets filled and suddenly tips over. Except the spilled water takes the form of jumbled thoughts in a new substack article.
Lessons learned over the past month, in no particular order:
Always be pushing
This doesn’t necessarily mean being pushy, but rather pushing for clarity. Asking follow-up questions if things are unclear or don’t make sense. Asking for proofs of commitment and advancement (h/t The Mom Test). Even things like being “pushy” in how you present yourself — framing yourself as an entrepreneur seeking feedback on your ideas or looking for an early partner/user. Even if “entrepreneur” is just one dude sitting in an apartment with no idea, team, or funding. And this is because…
People like entrepreneurs!
When I was starting out with customer discovery, I always worried about taking up people’s time. My tone was apologetic. I’m starting to come around to the fact that people generally like entrepreneurs. They know you build cool stuff that makes the world a tiny bit better, and if you succeed, maybe it can help make their life easier.
I noticed a step change in people’s responses to my emails when I went from presenting myself as a grad student looking to better understand the industry → grad student and aspiring entrepreneur hoping to improve XYZ process → early-stage founder looking to partner.
All of these are true characterizations, but the framing and implications are completely different. I think it’s crucial to get this right, because it has a big effect on the conversation, how they view you, and what they’re willing to offer.
When I changed my outbound emails to “early-stage founder looking to partner,” I was surprised that for the first time ever, the person I emailed was looping in their teammates. It became more of a pitch/sales/feel-out type of meeting, because now they knew that I wasn’t just trying to pick their brain. I could potentially help them. Same old me, very different results.
Getting stuck in limbo
It’s easy to deal with ideas that are obviously not getting traction or clearly getting traction. It’s the meandering, fuzzy, goopy stuff in the middle that’s the most problematic. I already know the answer here, which is Derek Sivers’ framework of “hell yes or no”. And yet I find this hard to do in practice. In hindsight, every time I find myself in limbo, I overthink it and let it drag on for too long.
There’s this chinese saying 食之无味,弃之可惜, often used to describe a chicken bone, that roughly translates into “when you eat it it has no flavor, but you also don’t want to throw it away”. A great description of being in limbo. And the reason this happens leads me to my next lesson:
The importance of countering your innate bias
I’m clearly biased in wanting my ideas to work. After a pretty brutal day of customer discovery calls recently, I still found myself debating whether the idea would work. Then I listed out the facts. There’s too many to name here, but the data point that really caught my attention was that my prospective customer (let’s call him Joe) had showed me a competitor’s tool, which was exactly what I envisioned mine would look like, replete with all the bells and whistles.
Joe’s company signed up for the tool a few weeks ago, but he hadn’t really tried it out yet. And that’s when it hit me. He had access to a solution that was at least 6-12 months ahead of mine, and hadn’t bothered to use it.
This is as negative of a signal as you can get. It’s hugely valuable, because it literally paints a picture of what my future will look like in 6-12 months if I continue down this path. It saved me a ton of time. And yet my brain had somehow done the substantial gymnastics to convince myself in the face of damning evidence, that perhaps the idea might not be so bad after all. Impressive.
Ruthless depth-first search
There’s always more work to do than time to do it. It gets pretty stressful sometimes when you think about everything you have to do, and try to keep track of all the balls in the air. But none of them really matter, except the highest-priority next item. It sounds extreme to put everything else in the backlog, but I suspect you wouldn’t be too badly off. Ruthless prioritization and depth-first search.
Being humble is a virtue. So is being confident. You have been very humble and considerate but in the face of truly getting to results and helping others, the pushing comes to help. Also said in the book “Never Eat Alone”, people are often willing to help and even feel glad for the chance to contribute. So don’t be afraid to ask for help or ideas. Overcoming innate bias and be laser focused are good traits to have too.