Steve Taplin is the CEO of Sonatafy Technology, author of “Fail Hard, Win Big: 30 Ventures | 20 Failures | 10 Wins,” and host of the Software Leaders Uncensored podcast.
In this conversation, Steve reveals the partnership that almost destroyed him but vindicated him five years later; why he walked out of a meeting with a Fortune 500 CIO; and the discipline that saved his sanity.
Steve also shares the 24-hour rule for processing failure to help his teams fail without breaking trust or morale. Steve breaks down the practice that taught him when to fight and when to quit.
If you’ve ever been paralyzed by the fear of failure—or worse, burned by a partnership you trusted—this episode will rewire how you think about risk, resilience, and what it actually takes to bounce back.
Find episode 501 on The Leadership Podcast, YouTube, or wherever you get your podcasts!
Watch this Episode on YouTube | Steve Taplin on Failure as Fuel: When to push through and when to quit
Key Takeaways
[04:02] Steve shares his most painful failure-turned-win: a $2 million deal his partner closed that he walked away from—five years later, both the partner and sponsor were indicted for fraud.
[08:21] Steve drops the hard truth: “Nobody cares about your business. They care about the problem it solves.”
[10:20] Steve’s philosophy on raising money: “Raising money is a responsibility—your business has to be ready for it.”
[12:09] Steve recalls his “oh sh*t” moment at IBM: he didn’t know the difference between sales and marketing after starting his first company.
[14:48] Steve credits journaling as his resilience tool and describes rehearsing failure scenarios with his team to build organizational resilience.
[2039] Steve defines earning potential: “Your ability to make money is your ability to solve more challenges than everybody else.”
[24:00] Steve recounts going back to IBM as VP of Sales and selling over $1 billion in contracts.
[29:52] Steve explains when to quit and the discipline that made financial clarity possible.
[38:13] Steve’s message to young people: “You don’t have a choice—the world is unforgiving. You either learn from failure or you don’t survive.”
[35:04] And remember…“Far better is it to dare mighty things, to win glorious triumphs, even though checkered by failure… than to rank with those poor spirits who neither enjoy nor suffer much, because they live in a gray twilight that knows not victory nor defeat.” – Theodore Roosevelt
Quotable Quotes
"Integrity is not optional, especially when you're raising money—it's foundational." Share on X "Nobody cares about your business. They care about the problem it solves Share on X "You get 24 hours to be upset. Then shake it off and figure out a solution." Share on X "Success is not just money—it's having the freedom to operate your business AND great relationships with your family." Share on X "Your ability to make money is your ability to solve more challenges than everybody else." Share on X "If you don't take risks, you can't keep accelerating your career." Share on X "Good, bad, or indifferent, you learn more from failures than you do successes." Share on X "You can't grow without failing." Share on X "Use your failures as fuel and learning experiences." Share on X "You got to know how to run businesses. You got to know how to sell if you want to take control of your life." Share on X
This is the book mentioned in this episode
Resources Mentioned
- The Leadership Podcast | theleadershippodcast.com
- Sponsored by | www.darley.com
- Rafti Advisors. LLC | www.raftiadvisors.com
- Self-Reliant Leadership. LLC | selfreliantleadership.com
- Steve Taplin LinkedIn | www.linkedin.com/in/stevetaplin
- Sonatafy Technology Website | www.sonatafy.com
- Software Leaders Uncensored YouTube | www.youtube.com/@SoftwareLeadersUncensored
- Software Leaders Uncensored Podcast | softwareleadersuncensored.com
Enjoyed this one, a lot. Thank you!