I find myself yearning to learn from CTOs who are a few steps ahead of me, only to realize that it’s not that useful when step 1 is so far away from step 0. So this newsletter is my attempt to document my process of getting to 1, no matter how long it takes my co-founder and I.
I quit my job at Slack as a staff software engineer a year ago now. It only gets harder to respond when people ask how your company is doing when you know you still haven’t reached PMF (product market fit).
At the beginning I had the classic naiveté of most first time founders (uninformed optimism). I figured if I could bring millions of dollars of value to Slack, how hard would it be to do it myself? Turns out very hard lol.
Here’s an overview of what my co-founder and I have worked on since quitting our jobs.
🪦 Failed Ideas
#1 Thinksy: Don’t lose another good idea (May - June 2023)
Thinksy saves & organizes your ideas directly in Slack so you don’t have to
Reason it Failed
Hard to sell (why would I pay for something that I can do for free in excel)
Didn’t nail a decision maker / buyer
Too generic / broad
#2 Thinksy: Performance reviews made easy (August - December 2023)
Reason it Failed:
Did not consider decision makers, interviewed SWEs who would use it but they couldn’t install because decision makers said no
Too many security concerns allowing a startup access to their messages / git commits AND still too early to trust OpenAI with their data
#3 Get to Staff (Jan - April 2024)
Reason it Failed
Did some research interviewing people who did formation and realized promotions aren’t as much as a pain point as getting a new job
Tried switching to helping people getting a new job, but people would only pay after you could guarantee they will get the job with your help (read: formation strategy)
Coaching was also hard to upsell without the ability to use company money (people don’t want to spend too much on their own career)
Ended up stopping because software didn’t seem to be the solution (although we are keeping the newsletter)
#4 Career Navi (Feb - April 2024)
Reason it Failed
Didn’t nurture this one enough to get the following required for this to be successful
Realized it was probably small potatoes comparing this to b2b saas
#5 Fortell (April - Jun 2024)
Reason it Failed:
Too small of a market
CFOs aren’t the ultimate decision makers of who gets this software (would be the CEOs)
#6 Keep Bufo Alive (July 2024)
Reason it Failed:
Didn’t really market and/or iterate on this mostly did it for fun lol
People didn’t really understand what they got out of giving money
#7 Keep Bufo Alive (iOS/Android)
Reason to Pivot:
Wouldn’t call this a failure because we had a lot of people loving our product, but we decided that we didn’t want to invest in a dying game format (hyper casual games)
Reflecting On Our Failures
With our first idea we were totally invested and made all the rookie mistakes:
Building out too early
Interviewing the wrong people
Not validating the market
Working on something we didn’t care about that passionately
We were extremely discouraged when our launch got us no money. We 180’d our ideas going forward to focus on what could get us money the fastest. Turns out that wasn’t the right move either. With a lack of focus or direction it was making us really depressed working on things not knowing if it helped us at all.
We eventually landed on sticking with a company, Flying Comet Games. We knew we wanted to do games and that direction was a sigh of relief. At least if we fail again it’ll be in the domain we care about.
Currently we’re working on making games for digital publishing. I’m not sure if that’s what we’ll stick with but I think we’re going in the right direction.
It’s easy for us to feel like we failed as founders last year but I have to remind myself how invaluable the lessons are from launching almost 10 products last year. My co-founder Calli and I are tenacious and we are more than willing to power through the valley of despair.
Here’s to 2025, the year of making shit people want!
Eden