I've bootstrapped 5 startups, and raised $6m in VC.
Here’s the key learning:
Customer obsession is EVERYTHING.
Startups today think customer support is a job for bots, scripts, or the cheapest VA you can find.
Let me say it for the people in the back:
If you’re outsourcing customer conversations before you’ve shipped a real product, you’re not building a company, you’re hiding from reality.
At BuddiesHR?
I was the support team.
If a customer had a problem, I was on it.
Day, night, holidays, whatever.
No tickets slipping through some offshore black hole.
No “your request is very important to us” corporate theater.
And 2 YEARS LATER, we STILL haven’t automated support.
Not because we’re lazy.
Because customer pain is gold.
Because those calls are how you learn what’s broken, what’s working, and how to actually get better.
Let’s get brutally honest:
1/ Founders want shortcuts to “scale,” so they stop showing up for their users.
2/ They brag about “AI-powered” support, but can’t answer a single real customer question themselves.
3/ They see support as a drain, instead of the only channel that gives a damn about their survival.
Truth:
You won’t build trust hiding behind technology.
You only get loyalty when you bleed for your users.
At BuddiesHR, obsession with every ticket, every call, every angry customer is the playbook.
That’s how you get traction when nobody cares about your logo.
That’s how you learn what nobody will put in a feedback form.
Serve customers or serve up excuses. There’s no middle ground.
You want to win?
Answer the phone.
Take the sh*t on the chin.
Ship the fix.
You want to lose?
Automate. Delegate. Disengage.
Still think “smart support” tools are your ticket to the big leagues?
Tell me how that worked out for your churn rate.
Because survival isn’t about scale.
It’s about obsession.
Disagree?
Show me your retention.
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👋 Hey, I'm J.Y!
I'm the co-founder of BuddiesHR, the #1 Employee Engagement Software that lives in Slack.
I post 1x a day about my journey and share what I've learned along the way.
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P.S. I'm writing a no-BS B2B SaaS playbook with everything I've learned. Want a free copy? Click “Visit my website” to sign up.