šŖ“ The founder's paradox
stay stubborn, yet flexible..
š Hi, Iām Oliver and welcome to my newsletter The Foundersā Fuel which is all about becoming a better startup founder. Join 10,153 founders and VCs backed by companies like a16z, YC, Accel, Sequoia, and more to gain data-driven insights, understand why they matter, and learn to use strategies that help your startup grow.
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I have a vision so clear it burns, a startup idea I would bet my life on. But markets shift, users surprise me, and new shit happens every single day.
Itās not easy. I have to stay stubborn, yet flexible if I want to make it out.
Every startupās heart is its mission. Paul Saffo says the Founderās Paradox is āholding that mission like a lifeline while staying ready to swap your playbook when data points to a better playā.
Itās about nailing our why, like making work seamless, but bending on the how, like jumping from software to services.
Steve Jobs crushed this at Apple. He lived for tech that felt human but pivoted from Macs to iPods when the market screamed music.
His vision held; his path didnāt. Stubborn, yet flexible.
We, founders, mess this up. Some of us cling to our original idea as something untouchable, even when thereās 0 traction. Why do we do this to ourselves?
Or we chase anything shiny. The founder paradox means we stand firm and pivot sharp in one breath.
Itās especially important in the last two years, when thereās too much happening with the AI boom. Startup closures increase, mainly because of this lack of āstubborness, yet flexibilityā.
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Slack is a textbook case of staying true to their vision, no matter the circumstances.
Stewart Butterfield started with a gaming idea but noticed users loved their chat tool more. He stuck to his why, seamless collaboration, but ditched games for enterprise software.
That pivot alone drove a $27B exit.
So what can we do to ensure this?
Pin your companyās why to one sentence, like āmake finances painless.ā
Every larger decision must align.
Track users and metrics daily, keep an eye on rivals. Test pivots small, like Slack did with its chat tool internally. Explain every shift to your team, tying it to the one-liner behind mission. Every quarter, check: is this path still the best bet?
Jeff Bezos mastered this at Amazon, staying customer-obsessed but flexing from books to global retail.
We get this right and we are golden.
Stay focused. Pivot sharp. Win slowly.
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