Ryan Walker 🚀


Sharing everything I learn

100 interviews in 100 days

Over the next 100 days I'm interviewing 100 people.

January 22, 20245 min read

Last Monday, the 15th January 2023, I started a new challenge to complete 100 discovery interviews in 100 days

My goal this year is to start building micro-startups, businesses that are bootstrapped, low-operational cost, generate recurring revenue from day 1 and most importantly solve at least one painful problem for a customer.

This is where the challenge comes in

I know that my strengths currently lie in execution, once I have the solution in mind I can usually figure out what needs to be done and do it. But my abilities fall short when it comes to recognising problems worth solving, this part of me has become blunt with years of putting solutions over the problems they're solving.

So over the next 100 days I'm going to try rewire myself to discover problems instead of solutions by interviewing 100 different people across a multitude of industries.

How it works

100 day challenges are fantastic whem I have one straightforward input that I can do every day and measure it, for example the last time I did this challenge I was learning to code, the input was the amount of time spent coding each day.

But interviews are not as straightforward, somedays I might not necessarily have a interview other days I might have more than one... Therefore the challenge by itself is currently an output metric and I'm not a fan of relying solely on output metrics, I think they're a terrible way to build habits and ultimately lead to almost certain failure because I'm not doing something productive towards the challenge each day.

To combat this I'm pairing the output metric of 100 interviews with an input metric of reaching outs to 3 prospective people each day. That means each day the main thing I need to do is reach out 3 people to hopefully this line up a backlog of interviews.

P.S If you're keen to chat! Send me an email, ryan.walkerz46@gmail.com

By the end of the challenge I will have reached out to at least 300 different people, with at least 100 of them turning into interviews.

First week down, how it's going

I originally wrote and published the first version of this blog last week, on the day I started the challenge but I couldn't bring myself to share it.

Maybe I didn't think it was the right challenge...

Maybe I was worried what other people would think...

Or maybe I didn't share it because decelerations of goals at this time of year usually fall to the same fate as New Years Resolutions... with 23% of people quitting their resolutions by the end of the first week (Why Most New Year's Resolutions Fail)

It wasn't any one of the above...it was really all of them and more. The art of putting myself out there AKA #BuildingInPublic is never easy, and I don't feel like I can do it just "right" so I turned inwards, I needed to prove to myself first that I could do this before sharing with the rest of the world.


The stats above are a snapshot of my progress over the last week

  • 23 people I reached out to
  • 12 of which replied to my initial outreach
  • 10 of those are booked in for an interview
  • 2 Interviews have already been complete

Honestly I'm proud of this first week, although I only interviewed 2 people so far, I learnt a lot about myself and what it's going to take to complete this challenge over the next 13 weeks for example:

Outreach is always hard...even when it's warm

The first few days were brutal, the sheer thought of messaging 3 people froze me in my digital tracks and it would take an entire day of putting it off before I finally hit send on those messages.

After those first few days, I've started to get into a rhythm that has sped up the task from taking all day to taking less than 30mins.

That lead to my next learning...

Outreach messages need to have a clear ask

I originally was worried if I asked people to chat with them upfront up I ran the risk of frightening them off so this initial message (below) was designed to warm up the idea then ask if they wanted to schedule a time to chat.

Hey X,


I’m doing a bit of research into the tools and software [THEIR INDUSTRY] are using. Just curious, have there been any tools you’ve been looking for over the last few months that you are having trouble finding for [THEIR COMPANY]?

As you can probably tell after my first 5 messages it became obvious that this was just confusing and I changed up the message as so:

Hey X,


A bit of a random favor but I’ve set myself a challenge this quarter to chat with 100 interesting people from various industries to learn more about what they do, the tools, problems, and intricacies. Down the line, this research may inform a product/service but for now, I'd love to catch up and chat with you a bit more about your experience in [THEIR INDUSTRY]

Let me know if you're interested and have some time free over the next few weeks for a quick chat.

This message is much clearer on what the ask is and it also drastically cut down the time from initial message to booking an interview.

but speaking of time between outreach and interview...

The delay between outreach and interview is real

I definitely underestimated how far out these interviews would be booked vs my initial outreach date. Most people prefer to have at least 1 week between booking a meeting and actually having it.

Fortunately if I factor this into my planning I can figure out how many interviews I need to be booking each week:

  • There are 14.2 weeks in the next 100 days
  • Minus the first week that has just passed and the final week, we're left with ~12 weeks
  • Assuming it takes on the average 7 days between initial outreach and interview scheduled
  • I need to be book at least 8+ interviews per week to hit my target of 100 interviews in 100 days

So, If you're keen to be interviewed! Send me an email, ryan.walkerz46@gmail.com 😅

As I wrap up this first week and look forward to the next, it's somewhat motivating to know, if almost one quarter of those who start New Years resolutions quit them before the end of the first week then by continuing on I've already achieved something can't wait to see what else is possible in the next 93 days.

I'll keep sharing updates on here about the journey, if you'd like to follow along you can stay in loop below.

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