When running Flywheel, I worked very hard to be right. Reflecting on the journey led me to the conclusion I frequently was right. But it wasn't enough and, explored below — not enough people knew.
Of course, I was also wrong. Likely more than I was right. Wrong about go-to-market ideas, UX designs, feature implementations... the list goes on. But as I look back, I think I was often right about new market opportunities.
Glossing over specifics, there were three separate milestones (1) where:
1.) I identified an adjacent market opportunity and specced the feature / product
2.) My team built the feature / product
3.) We "launched" the feature / product
4.) Competitors later released the same feature / product and got the market share
Quick aside: there are many reasons why this is how things played out. One is I'm selectively remembering when I was right (2). Two is that the markets didn't solve a real customer need. Three, differences in existing customer bases. Four, focusing on too many markets diluted all of our attempts. Let's set those aside for now. None of these, except for the last, should have prevented Flywheel from generating enough revenue to raise a Series A.
After pondering, the most likely explanation to the above is that when I was "right", I was "right" in silence.
Did you know I was right? Probably not. To you, Flywheel might not have ever even existed. You certainly didn't read about me on Hacker News, TechCrunch, or Product Hunt. And herein comes my regret; I was too afraid to be publicly wrong that I didn't try to prove I was right.
I gingerly subscribed to the adage of "build and they will come". Which is now explained ad nauseam to founders as the wrong path. Still, I convinced myself that the better product would win. And maybe it did and that product simply wasn't Flywheel. But to me, "build and they will come" was probably a convenient excuse to avoid being publicly wrong. It gave me permission to have tepid external convictions.
Now, to be very clear about the market trend examples above. The companies referenced did *not* change their roadmap due to our feature launches. They probably didn't even know we built them. The takeaway is that despite shipping the feature first, we lost any and all advantage by being quiet about it.
My wife and I regularly banter about the right way to open a boba shop. What should come first, good marketing or good boba? I've always been a staunch believer that it's the marketing. Get early design partners, tweak the product, then launch to a large waitlist. Typical B2B SaaS playbook.
Yet… why did I not follow my own advice? Why didn't I take the actions I argued are best? Whenever I reflect, my conclusion is that I was too afraid.
I don't consider myself to be fearful or timid. If anything, I would've said I was brash and overconfident at the time. But I still couldn't really put myself out there. Can I really say I would've marketed my boba first? Past history would tell me no.
Being quiet is not the reason Flywheel failed. At least, not the only reason. For brevity's sake I'm only investigating one factor. But this is a particularly frustrating factor. One where I felt like my actions (or lack thereof) matched almost 1:1 to the outcome. There was no market pressure, legislation change, or other external factor I can blame.
So yeah. If a tree is right in a forest and no one is around to hear it, was it ever really right?
(1). Integrating session replays into analytics, marketing intent alerts, account-based analytics.
(2). If I had been loud more often, I'm sure I would recall more of the times when I was wrong.
When running Flywheel, I worked very hard to be right. Reflecting on the journey led me to the conclusion I frequently was right. But it wasn't enough and, explored below — not enough people knew.
Of course, I was also wrong. Likely more than I was right. Wrong about go-to-market ideas, UX designs, feature implementations... the list goes on. But as I look back, I think I was often right about new market opportunities.
Glossing over specifics, there were three separate milestones (1) where:
1.) I identified an adjacent market opportunity and specced the feature / product
2.) My team built the feature / product
3.) We "launched" the feature / product
4.) Competitors later released the same feature / product and got the market share
Quick aside: there are many reasons why this is how things played out. One is I'm selectively remembering when I was right (2). Two is that the markets didn't solve a real customer need. Three, differences in existing customer bases. Four, focusing on too many markets diluted all of our attempts. Let's set those aside for now. None of these, except for the last, should have prevented Flywheel from generating enough revenue to raise a Series A.
After pondering, the most likely explanation to the above is that when I was "right", I was "right" in silence.
Did you know I was right? Probably not. To you, Flywheel might not have ever even existed. You certainly didn't read about me on Hacker News, TechCrunch, or Product Hunt. And herein comes my regret; I was too afraid to be publicly wrong that I didn't try to prove I was right.
I gingerly subscribed to the adage of "build and they will come". Which is now explained ad nauseam to founders as the wrong path. Still, I convinced myself that the better product would win. And maybe it did and that product simply wasn't Flywheel. But to me, "build and they will come" was probably a convenient excuse to avoid being publicly wrong. It gave me permission to have tepid external convictions.
Now, to be very clear about the market trend examples above. The companies referenced did *not* change their roadmap due to our feature launches. They probably didn't even know we built them. The takeaway is that despite shipping the feature first, we lost any and all advantage by being quiet about it.
My wife and I regularly banter about the right way to open a boba shop. What should come first, good marketing or good boba? I've always been a staunch believer that it's the marketing. Get early design partners, tweak the product, then launch to a large waitlist. Typical B2B SaaS playbook.
Yet… why did I not follow my own advice? Why didn't I take the actions I argued are best? Whenever I reflect, my conclusion is that I was too afraid.
I don't consider myself to be fearful or timid. If anything, I would've said I was brash and overconfident at the time. But I still couldn't really put myself out there. Can I really say I would've marketed my boba first? Past history would tell me no.
Being quiet is not the reason Flywheel failed. At least, not the only reason. For brevity's sake I'm only investigating one factor. But this is a particularly frustrating factor. One where I felt like my actions (or lack thereof) matched almost 1:1 to the outcome. There was no market pressure, legislation change, or other external factor I can blame.
So yeah. If a tree is right in a forest and no one is around to hear it, was it ever really right?
(1). Integrating session replays into analytics, marketing intent alerts, account-based analytics.
(2). If I had been loud more often, I'm sure I would recall more of the times when I was wrong.