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THEHARDESTTHINGTOGETRIGHT,
HOWIGOTITWRONG,
ANDWHATILEARNEDFROMIT.
Jordan Ritter
FOUNDER & CEO, IVY SOFTWORKS
MYBACKGROUND
A quick semi-illustrated primer
GROWIN’ UP
HIGHLIGHTS
Paid Hacker
Netect
Company acquired »
Golden handcuffs » Boredom
Founding Developer
Napster
Summer ’99 » Bay Area » Craziness
Founder, CEO » CTO
Cloudmark
Anti-spam » Messaging Security
CTO
Columbia Music
Music2 – Built a software incubator
inside a big Record Label
Founder, CTO
CloudCrowd » Servio
Modern crowdsourcing on
steroids
Founder, CEO
Ivy Softworks
A better model for building early
stage startups
• Tons of open-source stuff
• Nominated, Software Designer of the
Year, WIRED Rave Awards
• Interviewed in Playboy Magazine
• Taught a class at Harvard
OTHER FUN FACTS
THAT ONE TIME
A brief story about
(IT WAS ONLY ONCE, I SWEAR.)
• First true time off, thinking about
what’s next
• Random reconnect from a prior investor
• Beers, crowdsourcing,
and an instant vision
• He’d run the business,
I’d build the tech & team
BACKSTORY
Well…
SOUNDS PERFECT,
RIGHT?
• Dysfunctional culture
• Atmosphere of fear and mistrust
• Imbalance of power at BOD
• Tragic miss of a bigger opportunity
BIGGEST IMPACTS
FIRST, THE LOGIC OF
NOTACCEPTINGDEFEAT
Why I stuck with a bad partnership
OR,
Why I left
THEN, THE DECISION TO
ACCEPTDEFEAT
OR,
THELEARNINGS
And now,
• Will the tech work?
• Will anyone use the product?
• Will anyone pay for the product?
TYPICAL PROBLEMS I’M USED TO
DIAMONDMAKING
MACHINES
Startups are like…
+ ≈
MARRIAGES
Startups are like…
EMOTIONAL
ROLLERCOASTERS
Startups are like…
YOUWILL
SUFFER
(And boy does it suck to be alone in your suffering!)
• Raise money
• Find talent
• Engineer the product
• Market the products and company
“Ugh, if only I could find someone to…”
• Run operations
But…
ITISBETTERTO
ITISBETTERTO
SUFFERALONE
ITISBETTERTO
SUFFERALONE
THANTO
ITISBETTERTO
SUFFERALONE
THANTO
SUFFERWITHFOOLS
But…
WITHTHE
WITHTHE
RIGHTPEOPLE
WITHTHE
RIGHTPEOPLE
YOUWILL
WITHTHE
RIGHTPEOPLE
YOUWILL
SUFFER HAPPILY
• Always interview for values first
• Critical Thinking > Problem Solving
3 C’s: Culture, Capacity, Craft
• Capacity for Mastery > Current Skills
ALRIGHT THEN, HOW?
IN CONCLUSION
• Make peace with doing it all, by yourself
(at least once)
• Define values early & stay true to them
• Master how to evaluate values in others
THE HARDEST THING: PEOPLE
• Suffer happily, or choose to stop suffering
(IT CAN BE THAT EASY)
THANKS
FOR
LISTENING
jpr5@ivysoftworks.com

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The Hardest Thing To Get Right (GeekWire Startup Day 2015)