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Most Entrepreneurs Suck at Hiring.
Keith Tessler learned a lesson most founders eventually figure out the hard way: Technology isn’t the hard part. People are.
In this episode, Steve Cross sits down with Keith Tessler, CEO of CMIT Solutions, to talk about getting thrown into leadership in his 20s, helping modernize a family business during the PC revolution, learning leadership through mistakes, and building an IT company without creating a burnout culture in the process.
They also get into cybersecurity, AI, scaling service businesses, hiring failures, company culture, and why entrepreneurship eventually turns into a sales job whether you like it or not.
About Our Guest
Keith Tessler is the CEO of CMIT Solutions, an outsourced IT and cybersecurity company serving small and mid-sized businesses. Before launching CMIT Solutions, he spent 24 years helping grow a nationwide wedding and media company before moving into executive coaching and eventually returning to entrepreneurship to build his own MSP practice.
About Success Stories
Welcome to Success Stories, the podcast where Steve Cross sits down with the sharpest minds in business to unpack what it really takes to grow.
From scrappy upstarts to category leaders, each conversation reveals the mindset, strategies, and personal stories behind bold decisions and breakthrough moments. No fluff. No gurus. Just real founders, real operators, and real results.
If you're a growth-obsessed entrepreneur, marketing leader, or future founder, this playlist is your shortcut to hard-earned wisdom from those who've built it, scaled it, and lived to tell the tale.
👉 Subscribe to the channel and hit the bell so you never miss an episode.
👉If you think you can hang, this link is for you. https://stevecross.wtf
👉 For more about iSynergy and how we help brands grow through strategic digital marketing, visit https://isynergy.io/connect/.
#SuccessStories #Entrepreneurship #Leadership #Cybersecurity #BusinessGrowth #MSP #AI #FounderStory #SmallBusiness #BusinessPodcast #CompanyCulture #Sales #Hiring #EntrepreneurMindset #TechLeadership
View all episodes
By Steve CrossKeith Tessler learned a lesson most founders eventually figure out the hard way: Technology isn’t the hard part. People are.
In this episode, Steve Cross sits down with Keith Tessler, CEO of CMIT Solutions, to talk about getting thrown into leadership in his 20s, helping modernize a family business during the PC revolution, learning leadership through mistakes, and building an IT company without creating a burnout culture in the process.
They also get into cybersecurity, AI, scaling service businesses, hiring failures, company culture, and why entrepreneurship eventually turns into a sales job whether you like it or not.
About Our Guest
Keith Tessler is the CEO of CMIT Solutions, an outsourced IT and cybersecurity company serving small and mid-sized businesses. Before launching CMIT Solutions, he spent 24 years helping grow a nationwide wedding and media company before moving into executive coaching and eventually returning to entrepreneurship to build his own MSP practice.
About Success Stories
Welcome to Success Stories, the podcast where Steve Cross sits down with the sharpest minds in business to unpack what it really takes to grow.
From scrappy upstarts to category leaders, each conversation reveals the mindset, strategies, and personal stories behind bold decisions and breakthrough moments. No fluff. No gurus. Just real founders, real operators, and real results.
If you're a growth-obsessed entrepreneur, marketing leader, or future founder, this playlist is your shortcut to hard-earned wisdom from those who've built it, scaled it, and lived to tell the tale.
👉 Subscribe to the channel and hit the bell so you never miss an episode.
👉If you think you can hang, this link is for you. https://stevecross.wtf
👉 For more about iSynergy and how we help brands grow through strategic digital marketing, visit https://isynergy.io/connect/.
#SuccessStories #Entrepreneurship #Leadership #Cybersecurity #BusinessGrowth #MSP #AI #FounderStory #SmallBusiness #BusinessPodcast #CompanyCulture #Sales #Hiring #EntrepreneurMindset #TechLeadership