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

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'TSHarpreet Singh, Co-CEO Launchable — on the mistake that erodes confidence in leadership faster than anything elseJosh Ellars, CEO OpenGTM — on the decision he kept making wrong, more than onceEd Bradley, CEO Virtualstock — on why being turned down by every investor was the best thing that happened to himEmeric Ernoult, CEO Agorapulse — on the reason he almost gave away part of his company for nothingKrishna Raj Raja, CEO SupportLogic — on which hiring mistake is actually more dangerousJason Cohen, Founder WPEngine — on the belief that quietly kills more scaling companies than anything elseDO'SMatt van Itallie, CEO Sema — on why the leadership book's answer didn't workRichard White, CEO Fathom — on what the best YC founders had in common that surprised himMatt Achariam, CEO Mesh — on what falls apart when momentum arrives too fastScott Reynolds, CEO UpCodes — on the question most AI founders can't answerMark Walker, CEO Nue — on why creating a new market isn't always the best ideaCaitlin MacGregor, CEO Plum — on why CEOs should spend more time sellingTal Peretz, CEO Onfire — on saying no to customers who wanted to pay himJason Cohen, Founder WPEngine — on the one thing worth fixing before everything elseEmeric Ernoult, CEO Agorapulse — on why testing for the outcome is the wrong testTheo Saville, CEO CloudNC — on the difference between a busy team and a focused oneRandy Wootton, CEO Maxio — on what nobody tells you before you sit in the CEO chairJon Jorgensen, CEO The Access Group — on how he actually went about finding the right peopleDinakara Nagalla, CEO EmpowerMx (acquired by IFS) — on what remarkable actually means when nobody is watching