🙈5 Startup Lessons I Learned The Hard Way🙈
6m ago I left as CTO/co-founder of my first startup. We'd been nose-to-the-grindstone for the last 2+ years but results weren't close to expectations.
Here are my biggest mistakes & takeaways so that hopefully you avoid them.
👇
6m ago I left as CTO/co-founder of my first startup. We'd been nose-to-the-grindstone for the last 2+ years but results weren't close to expectations.
Here are my biggest mistakes & takeaways so that hopefully you avoid them.
👇
1/ Validate obsessively before you build.
Does the problem ACTUALLY exist?
How deeply do customers feel this pain?
Would they pay for it?
We obsessively built before we tested.
We idolized our "original vision."
This is the #1 most expensive mistake first-time founders make.
Does the problem ACTUALLY exist?
How deeply do customers feel this pain?
Would they pay for it?
We obsessively built before we tested.
We idolized our "original vision."
This is the #1 most expensive mistake first-time founders make.
Read: nfx.com/post/new-minds…
@GigiLevy has forever changed me as a founder.
Unfortunately I read this too late. I learned the hard way that u gotta find product-PROMISE-market fit first.
The longer ur deal cycle, the costlier it gets to skip validation. Mine was 9-12 months!
@GigiLevy has forever changed me as a founder.
Unfortunately I read this too late. I learned the hard way that u gotta find product-PROMISE-market fit first.
The longer ur deal cycle, the costlier it gets to skip validation. Mine was 9-12 months!
2/ Be sales-driven, not product-driven.
Here's a diagram from @HuaNancy. It divides startups into 4 quadrants: hard/easy to sell, hard/easy to build.
(i.e. What type of game are u playing?)
Optimizing to win begins with knowing what game you're even playing in the first place.
Here's a diagram from @HuaNancy. It divides startups into 4 quadrants: hard/easy to sell, hard/easy to build.
(i.e. What type of game are u playing?)
Optimizing to win begins with knowing what game you're even playing in the first place.
Sounds duh.
But we got it wrong.
We thought we were quadrant IV (hard to build, easy to sell). We were actually quadrant I (hard both).
We were an enterprise sales company who didn't understand consultative sales.
We thought we could focus 200% on development; 5% on deal funnel.
But we got it wrong.
We thought we were quadrant IV (hard to build, easy to sell). We were actually quadrant I (hard both).
We were an enterprise sales company who didn't understand consultative sales.
We thought we could focus 200% on development; 5% on deal funnel.
The combo of not validating first AND not knowing how to do consultative sales was toxic. Not only did we not understand our customer demands from day #1; we made it impossible to learn over time!
Lessons:
- ask more questions; pitch less
- customize; plug-n-play is a myth in B2B
Lessons:
- ask more questions; pitch less
- customize; plug-n-play is a myth in B2B
3/ Founder-market fit.
Here I was running a cyber risk modeling startup but didn't have the network of a Unit 8200 Israeli Massader.
Relative to many other cyber startups, we were massively disadvantaged in our ability to attract talent & establish industry partnerships.
Here I was running a cyber risk modeling startup but didn't have the network of a Unit 8200 Israeli Massader.
Relative to many other cyber startups, we were massively disadvantaged in our ability to attract talent & establish industry partnerships.
4/ Co-founder fit.
There are only 2 good reasons founders should pair up:
1. personal compatibility (will stick together through big pivots)
2. business compatibility (skillsets & network are a match specific to THIS problem)
IMO, unless someone checks BOTH boxes, stay single!
There are only 2 good reasons founders should pair up:
1. personal compatibility (will stick together through big pivots)
2. business compatibility (skillsets & network are a match specific to THIS problem)
IMO, unless someone checks BOTH boxes, stay single!
Max likelihood outcome of #1 w/out #2 is you'll pivot a bunch & run slower than a team that has founder-market fit.
Max likelihood outcome of #2 w/out #1 is the company splits. Most likely ur visions aren't perfectly aligned. Imagine if your two legs each had minds of their own.
Max likelihood outcome of #2 w/out #1 is the company splits. Most likely ur visions aren't perfectly aligned. Imagine if your two legs each had minds of their own.
Last important note on team structure:
Having the right network but not skillset makes for a great advisor (not a great cofounder). This person may be super high-value to the company but their value doesn't increase when they stick around day to day.
Having the right network but not skillset makes for a great advisor (not a great cofounder). This person may be super high-value to the company but their value doesn't increase when they stick around day to day.
5/ Division of roles.
As founders we hear all the time that u gotta "wear multiple hats." That's awesome until u come across a hat that fits 2 heads. Who takes point?
Hesitate too long and the ball ends up rolling down the middle untouched.
Or you both pounce & do double work.
As founders we hear all the time that u gotta "wear multiple hats." That's awesome until u come across a hat that fits 2 heads. Who takes point?
Hesitate too long and the ball ends up rolling down the middle untouched.
Or you both pounce & do double work.
I was CTO but didn't want to be.
I was doing things I wasn't awesome at, and not doing things I was awesome at.
Not leading sales gnawed at me; my reluctance made me a terrible eng manager. My team told me that trying to get big-picture context from me was like pulling teeth.
I was doing things I wasn't awesome at, and not doing things I was awesome at.
Not leading sales gnawed at me; my reluctance made me a terrible eng manager. My team told me that trying to get big-picture context from me was like pulling teeth.
My story has a happy ending!
I'm building a new startup now-- a tool for retail traders like you and me!💗
Today's capital markets are built for hedge funds, not us individuals. Let's change this!
Expect a beta release in December! I'll be documenting pieces of my journey here!
I'm building a new startup now-- a tool for retail traders like you and me!💗
Today's capital markets are built for hedge funds, not us individuals. Let's change this!
Expect a beta release in December! I'll be documenting pieces of my journey here!
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