On the TechTO, TechVancouver & TechWaterloo stages ×4
Stuff I Learned Doing Startups
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Stuff I Learned Doing Startups
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Trials and Tribulations of Scaling Your Tech Startup (panel with Kim Kaplan)
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The #1 Thing to Being Happy and Successful
Watch on YouTube ↗First seen on the TechTO, TechVancouver & TechWaterloo stages in 2016. Every talk is searchable — ask the archive about Neil ↗
In their words
Happy relationships are the number one reason for longevity and success and everything else in life.
That equity that you give away along the way when you're growing your business is incredibly expensive.
Part of our core values is 'make new mistakes' — that's literally what we call it. I tell people if they're not making mistakes, they're not trying hard enough.
the tech companies I see that get into trouble is because they stop developing their technology
if we had stayed true to our what we started out with we would have missed what we became because we didn't we wouldn't have pivoted
sell to Americans first
Early cash is very expensive if you can do it great but if you can't bootstrapping is good.
When products get stale Revenue doesn't climb when Revenue doesn't climb you don't have money to invest in the product it becomes this Vicious Circle where you can't get out of it.
You have to have a path to making money or you're just going to be consuming money until you have no equity left because you keep giving it away to get more cash.
Around the web ×1
Quick answers
What was UpHabit?
His eighth startup, an app for remembering the people and companies in your network — he said he started it because he kept forgetting company names. At the February 2019 TechVancouver panel it was two weeks from launch; by his January 2020 TechTO talk he was CEO with an engineering team recruited largely from abroad (Lebanon, Brazil, Dubai, Russia) and brought to Canada. The service shut down in April 2026.
What was Nexonia and how did it end?
An expense-management SaaS he co-founded in 2002, which began as timesheets and expense reports for consulting firms. Bootstrapped for its first 13 years, it doubled annually for five years to about 2,000 corporate accounts — Splunk, Marketo and Slack among them — with negative 30 percent net churn. He sold control to private equity in May 2016 after 14.5 years as CEO; three weeks later the new owners let him go, a right he says they had paid for.
What does he say is the key to being happy and successful?
Relationships. His 2020 TechTO talk cites a 75-year Harvard study and the regrets of the dying to argue happy relationships drive longevity and success. His Peerscale CEO group proved it in practice: they told him to tear up his first term sheet, which added an extra five million dollars to his exit. Citing Adam Grant's Give and Take, he advises giving help before expecting anything in return.