In this episode of the Revenue Builders podcast, returning guest Doug Holladay joins the show to explore why forgiveness is not just a personal virtue, but a critical leadership skill. Drawing from Doug’s book Rethinking Success and decades of leadership experience, the conversation reframes forgiveness as a way to reclaim mental bandwidth, build trust-driven cultures, and prevent resentment from quietly eroding performance. The discussion moves beyond theory into real stories, practical distinctions, and leadership behaviors that directly impact how teams operate and scale.

Doug Holladay is an author, educator, and leadership advisor known for helping leaders examine the internal patterns that shape culture, decision-making, and long-term success. He is the author of Rethinking Success and a frequent contributor to conversations on leadership, humility, and organizational health.

Resources mentioned:

• Rethinking Success by Doug Holladay
• The Wounded Healer by Henri Nouwen
• What Happened to You? by Bruce Perry and Oprah Winfrey

Key takeaways from this episode:

• 01:33 Why holding onto resentment quietly drains a leader’s focus, energy, and decision-making capacity
• 10:45 What most leaders get wrong about culture, and why how you handle conflict matters more than what’s written on the wall
• 12:28 The difference between forgiveness and reconciliation -- and why waiting for an apology keeps leaders stuck
• 23:34 What forgiveness actually looks like in real leadership moments (and why it’s not about fairness or closure)
• 26:44 Why leaders who avoid examining their own role in conflict rarely move forward – even when they’re “right”
• 35:42 Why humility isn’t weakness -- and how strong leaders redirect power instead of using it defensively
• 49:13 How shifting from “What’s wrong with them?” to “What happened to them?” changes the way leaders respond under pressure

Hosted by five-time CRO John McMahon and Force Management Co-Founder John Kaplan, the Revenue Builders podcast goes behind the scenes with the sales leaders who have been there, done that, and seen the results.

This show is brought to you by Force Management. We help companies improve sales performance, executing their growth strategy at the point of sale.

Connect with Us:

• LinkedIn
• YouTube
• Force Management

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Don't miss these resources from Force Management:

• Read the Guide on Six Critical Priorities for Revenue Leadership in 2026: https://hubs.li/Q03JN74V0
• Enjoying the podcast? Sign up to receive new episodes straight to your inbox: https://hubs.li/Q02R10xN0

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

In this short segment of the Revenue Builders Podcast, HubSpot co-founder Brian Halligan pulls back the curtain on the uncomfortable truth of scaling: there is no magic inflection point—only relentless progress, painful setbacks, and self-inflicted potholes. Brian shares how HubSpot embraced a “Pothole Report” mindset to identify unforced errors before they became existential threats, why most scaling failures are internal, and how long-term thinking—not quick exits—shaped HubSpot into a generational company. It’s a masterclass in founder mindset, operational discipline, and playing the long game in hypergrowth.

KEY TAKEAWAYS

[00:00:25] There is no magical hire, partnership, or customer that suddenly fixes everything—success is a grind, even in the best moments
[00:01:13] The road to scale is filled with setbacks, many of which are self-inflicted rather than caused by competition
[00:01:58] The “Pothole Report” helped HubSpot systematically identify mistakes, root causes, and missing metrics before small issues became big failures
[00:02:32] Promoting too fast without protecting core functions can quietly break critical systems like customer support
[00:03:27] In hypergrowth, people, systems, processes, and products don’t scale naturally—everything eventually breaks
[00:04:28] No system, process, or role lasts more than three years without needing to be rebuilt or replaced
[00:05:12] Contrary to startup mythology, acquisition opportunities are rare—even for successful, fast-growing companies
[00:06:20] Founders often optimize for “local maxima” instead of anchoring their ambition against truly global category leaders
[00:07:17] Aligning founder expectations early—especially around time horizon and exit scenarios—enables long-term conviction and focus

QUOTES

[00:00:25] “Every happy moment’s been a grind.”
[00:01:13] “So many setbacks along the way. So many unforced errors.”
[00:01:58] “Here’s all the potholes we have—and almost all of them we caused ourselves.”
[00:03:27] “In hypergrowth mode, nothing scales. Everything breaks.”
[00:04:44] “No person lasts longer than three years. No system, no process, no nothing.”
[00:06:42] “We wanted to build a company our grandkids would be proud of.”
[00:07:36] “We’d already made some money—so we decided to swing hard.”

Listen to the full conversation through the link below.
https://revenue-builders.simplecast.com/episodes/innovating-and-iterating-for-growth-with-hubspot-co-founder-brian-halligan

Enjoying the podcast? Sign up to receive new episodes straight to your inbox:
https://hubs.li/Q02R10xN0

Check out John McMahon’s book here:
Amazon Link: https://a.co/d/1K7DDC4

Check out Force Management’s Ascender platform here:
https://my.ascender.co/Ascender/

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.