So You Want to Be a Founder?

I am not (yet) a successful founder, so take what I say with a grain of salt. However, there are a few lessons I want to share.

So You Want to Be a Founder?
So You Want to Be a Founder?

I have spoken to many founders about what it is like starting a company. When listening to founders talk about their early days, they give off a romantic sense of fearlessness, coupled with a clear sense of direction, followed ultimately by success (this is what we call selection bias). Even when they inevitably launch into anecdotes about late nights, server outages, and customer horror stories, it never seems like they questioned whether each obstacle was the correct one to be addressed at that point in time. But in my experience, this isn’t even close to being true.

Now, two months into my own founder journey, I’m learning that these David-vs-Goliath stories skip over the daily process of re-evaluating what is important, the sure-things washed away with a single email, the sheer amount of luck involved in starting a company, the amazing (and not so amazing) people willing to help, and the constant state of not knowing which direction the finish line is in – or if there even is one.

I am not (yet) a successful founder, so take what I say with a grain of salt. However, there are a few lessons I stumbled upon that I want to share:

Two things happen the moment you quit your day job to go full time on your founder journey:

1. Your LinkedIn inbox gets flooded with spam from every service provider you could imagine (no, I do not have time this week to hop on a quick intro call) and,

2. The sudden waterfall of to-dos starts pouring over your head.

While I can’t help you avoid the LinkedIn spam, I found a few mental models and practices to deal with number 2 so you can avoid feeling like Sisyphus.

  • Sit and think as often as possible - Preferably in a quiet place without a toddler. Eventually, you won’t have time during your day to let your mind wander about ideas. So make space for this type of thinking, as it is likely what got you to this point in the first place.
  • Product reflection - Keep asking why people will care. Don’t buy into your own marketing or sales pitch as the truth. Every time you pitch your product, evaluate your listeners' reactions. Are they falling asleep as you start speaking, or do their eyes light up as you lay out your idea?
  • Self-reflection - Keep asking what your weaknesses are and keep looking for bottlenecks in your team's process. Find where you are the limiting factor and correct the issue. This usually involves abdicating work to another team member.
  • Timebox everything - Otherwise, you don’t get the right things done. Each week, I sit down and block out deep work periods to tackle the 2-3 largest items. Ironically, the 2-3 most pressing items change every single day, so adjust accordingly.
  • Ask for help on all things out of your expertise – This ties into self-reflection but goes a step further to seek outward help where necessary. For me, this was bookkeeping and marketing. There are other things I am not great at, but these two were obvious for me to start.
  • Listen selectively – Many people will start offering advice to you simply because you have the title “Founder” in your LinkedIn profile. Listen to them, ask them about their experiences, but be mindful of the context.
  • Sourcing candidates is harder than ever - And I’m saying this as the founder of a hiring and recruiting tech company! Get your messaging right. People want to know who is soliciting them and why they should care. Keep asking yourself why people will care about what you are doing – and be mindful that most people won’t care initially.
  • Most importantly, put trust in your first hires. But don’t do this blindly, or you will set them up for failure. Ensure you have given them the tools to run with things and execute.

Lastly, here are a few things I am still trying to remind myself to do as I move deeper into my founder journey:

  • Constantly ask whether I’ve got the right data - Simple things like Google Analytics, Stripe events, click events in your app, etc. are necessary to make the right decisions. Data-oriented decisions are the key to success; incorrectly capturing data and making subsequent poor decisions lead to failure. Set your metric north stars – monitor and re-evaluate periodically to make sure you are still aiming in the right direction.
  • Talk to people constantly - Practice your elevator pitch (drop the stealth-mode nonsense). Get in reps by bringing it up in normal daily conversations. Seek brevity and precision.

In two months Chatkick’s elevator pitch has gone from:

“Chatkick helps teams scale their interview process by letting teams to record, transcribe, and analyze their candidate screenings. With an interactive video interview platform, hiring managers can be sure every candidate screening is being done consistently. Chatkick offers distributed teams a way to asynchronously review and collaborate on candidate feedback.”


“Interview management for distributed teams.”

It is not that founder stories fail to mention all of these things, it is that these things tend to appear in everyone’s narrative in slightly different ways. While the first few weeks and months of a startup are exhausting, it is always a good reminder that Rome wasn’t built in a day...although I am damn sure they were laying bricks every single day.