#400 - What 99 CEOs wish they'd known sooner

About this episode

In this milestone episode, Ton Dobbe shares 18 key insights from 99 CEOs about the lessons learned in building successful software companies.

Four hundred episodes. When I started this podcast, I had one simple belief: the best lessons in building a remarkable software company don't come from business books or consulting frameworks. They come from CEOs who've lived it — the ones who made the hard calls, paid for the wrong assumptions, and built something worth talking about. I went back through the last 99 conversations — and pulled the 18 insights that I believe will genuinely open your eyes. Not the ones that make you nod. The ones that hold a mirror. I selected them for one reason: each one connects directly to the traits I write about in The Remarkable Effect . The patterns that separate the software companies people keep talking about from the ones that quietly disappear. Six don'ts. Twelve do's. The don'ts follow one thread — each one is an assumption that ended up costing a CEO everything. The do's move from the inside out — who you need to be, how you compete, how you grow, and who you put around you. Here's who you'll hear from: DON'TS Harpreet Singh, Co-CEO Launchable — on the mistake that erodes confidence in leadership faster than anything else Josh Ellars, CEO OpenGTM — on the decision he kept making…

People in this episode

Host: Ton Dobbe

Guests: Harpreet Singh, Josh Ellars, Ed Bradley, Emeric Ernoult, Krishna Raj Raja

Topics covered

• CEO insights
• business lessons
• software companies
• leadership mistakes
• growth strategies

Keywords

• CEOs
• business lessons
• leadership
• software
• growth

Mentioned in this episode

Organizations: Launchable, OpenGTM, Virtualstock, Agorapulse, SupportLogic

More episodes of The Remarkable SaaS Podcast

• #407 – How Martin Gourdeau refused the commodity race and added $1M ARR in 9 months · June 10, 2026 · 52 min
• #406 – How Chad Gaydos chose fit over TAM and doubled deal sizes in 12 months · June 3, 2026 · 45 min
• #405 – Burak Karakan, CEO of Bruin - On the cost of trying to please everyone · May 27, 2026 · 58 min
• #404 – How Tim Barker proved the software org chart is now optional · May 20, 2026 · 51 min
• #403 – Why Amos Bar-Joseph rejected the playbook every unicorn ran · May 13, 2026 · 40 min
• #402 – How Joseph Lee refused to outspend his rivals — and outgrew them anyway · May 6, 2026 · 45 min