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221: Why Fear of Success Holds You Back More Than Failure | John Golden

Episode 221

In this high-energy episode of The Learn-It-All Podcast, host Damon Lembi is joined by John Golden, Chief Strategy and Marketing Officer at Pipeline CRM and host of the SalesPop podcast. Together, they dig deep into the art of decision-making, the power of authenticity in leadership, and the lessons learned from the dot-com era—offering actionable advice for anyone looking to future-proof their business or career. John shares personal stories about trusting his gut, being deliberate with growth, and why admitting you don't know is the ultimate mark of expertise. From the importance of resilience and learning from mistakes, to navigating VC/PE relationships and thriving in an AI-driven world, this episode is packed with wisdom for founders, leaders, and ambitious professionals alike.

In this episode, you’ll learn:

Why authenticity—not bravado—is the key to earning trust as a leader
How to assess “the why” behind big career or business decisions (and how John’s gut instinct saved him from a bad move)
What founders and business leaders today can learn from the triumphs and failures of the dot-com boom and bust
Smart, intentional ways to grow your company without overextending (including when and how to bring on VC/PE partners)
Why being willing to admit mistakes—and learn from them—sets the best leaders apart
How “fractional” and contractor talent can turbocharge your business without risky overhead

Timestamps

00:00 – The power of admitting mistakes and authentic leadership

01:09 – Why you’re never 100% ready: advice for big leaps

03:46 – When “the why” isn’t strong enough: a dot-com era cautionary tale

07:01 – Should you take the “wrong” job just to pay the bills?

08:08 – John’s move to Silicon Valley: seizing unexpected opportunities

09:34 – Lessons from the dot-com boom and bust (and AI parallels)

14:58 – Practical advice for founders: bootstrapping, VC/PE diligence, and controlled growth

18:37 – Balancing gut instinct with due diligence

20:56 – Leveraging fractional, contract, and remote talent strategically

22:51 – John’s pivotal career moment: setting your sights on the CEO role

25:01 – Why (and how) people limit their own potential

27:54 – Overcoming fear of failure—and fear of success

29:29 – Imposter syndrome and why you should apply for the job anyway

30:27 – The value of authenticity (and how to show it as a leader)

32:20 – Failing forward: why mistakes are fuel for growth

33:58 – The value of humility and vulnerability in leadership

35:11 – Where to connect with John and find SalesPop

About John Golden

John Golden is the Chief Strategy and Marketing Officer at Pipeline CRM and the host of SalesPop, a podcast with over 1,500 episodes featuring top leaders and sales innovators. With a distinguished background in sales strategy and executive leadership, including experience navigating the boom and bust of Silicon Valley’s dot-com era, John is known for his candid, authentic approach to business. He specializes in helping founders and business leaders future-proof their organizations by building on solid fundamentals, leveraging gut instinct, and hiring resilient, authentic teams.

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Published on 2 months, 2 weeks ago

Podcast Episode Details

221: Why Fear of Success Holds You Back More Than Failure | John Golden