Don’t Do That: The Best "Don't Do That" Moments from Industry Leaders
Summary:
What if the secret to success isn’t what you should do, but what you absolutely shouldn’t?
What do brilliant jerks, head trash, and the “parent thing” have in common? They’re all career killers that successful leaders have learned to avoid (the hard way).
Kelly Waltrich curates the most eye-opening “don’t do that” moments from 20+ industry titans who’ve made every mistake so you don’t have to. This isn’t your typical highlight reel; it’s a rapid-fire collection of expensive lessons learned, toxic patterns exposed, and blind spots revealed.
In just 21 minutes, you’ll get decades of collective wisdom from leaders who’ve scaled companies, survived failures, and discovered what actually moves the needle. These are battle-tested insights from the trenches of real business, distilled into the exact moments that changed everything for these executives.
Featured wisdom covers:
- Why brilliant jerks are organizational poison (and how to spot them)
- The dangerous allure of inorganic growth over organic foundations
- How collecting “head trash” sabotages your leadership
- Why the best idea doesn’t always win
- The critical difference between being known and being worth knowing
Timestamps:
00:00 – Introduction: Why “don’t do that” wisdom matters
00:44 – Adam Holt, Asset-Map: Don’t assume you know what customers really want “Are we asking our clients what they really, really want?”
01:41 – Eric Clarke, Orion: Don’t underutilize AI for client relationships Using AI only for meeting notes misses massive opportunities
02:32 – Ainslie Simmonds, BNY Pershing: Never hire a brilliant jerk “They’re poison… when they sneak in, get them out quick”
03:16 – Chris Schembra, 7:47: Don’t chase recognition; be worth knowing Achievement for achievement’s sake will never be as fulfilling as doing the work
03:54 – David Wood, Gateway Financial Partners: Don’t go it alone at scale Why successful firms invest in resources and partnerships
04:37 – Billy Hopkins, Silver Oak Securities: Don’t think small when opportunity knocksHow holding on too long or limiting your sphere kills growth
05:08 – John Wernz, Great Hill Partners: Don’t prioritize inorganic over organic growth The seductive trap of acquisition math vs. building solid foundations
06:07 – Marwa Zakharia, MZ Global Consulting: Don’t lead by pointing out what’s wrong“You built a phenomenal rocket. That doesn’t mean you need to be the one flying it”
06:55 – Heather Fortner, SignatureFD: Stop collecting other people’s “head trash” Why internalizing others’ negativity sabotages your leadership
08:00 – Jason Mirabella, Intention.ly: Don’t dictate initiatives from the top down Get stakeholders involved early or risk creating adversaries
08:44 – Randy Lambert, Intention.ly: Don’t do the “parent thing” with leadership Bring data and facts, not “the CEO said this”
09:17 – Jack Sharry, SEI LifeYield: Don’t wait for your turn to talk “Listen so hard you burn calories”
10:01 – Brian Portnoy, Shaping Wealth: Don’t believe the best idea always wins Why sales and connection matter more than pure brilliance
10:44 – Penny Phillips, Journey Strategic Wealth: Don’t listen to too many people How polling everyone kills your instinct and power
11:55 – Chris Shuba, Helios: Don’t fall in love with your solution Love the problem, not your solution—because problems evolve
13:19 – Sara Baker, Allworth Financial: Don’t measure work-life balance in weekly increments Think in yearly timeframes for true perspective
14:05 – Joel Bruckenstein, T3: Don’t believe you’re a master of everything Why trying to do it all yourself limits greatness
14:53 – Mark Gilbert, Zocks: Don’t delay marketing and selling Product love isn’t enough—marketing is a skill that takes time
15:50 – Jamie Hopkins, WSFS Bank: Don’t compare yourself to averages Find best-in-class benchmarks, not mediocre standards
16:39 – Jason Early, RISR: Don’t let bad news age “Say the thing you think you cannot say”
17:45 – Adrian Johnstone, Practifi: Don’t shoulder all decisions alone (but don’t be paralyzed either) Consult widely, then have courage to decide
18:48 – Molly McClure, Intelliflo: Don’t hire experts and then micromanage them Trust the talent you bring in to do what they do best
20:16 – Closing thoughts and next steps
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About This Episode:
This compilation represents the collective wisdom of over 20 industry leaders who’ve learned expensive lessons so you don’t have to. Each “don’t do that” moment comes from real experience—the kind of hard-won insights that typically cost years of trial and error.
From technical founders to seasoned executives, these leaders share the mistakes that shaped them and the wisdom that defines their success. Whether you’re building your first team or scaling your tenth company, these insights offer shortcuts to better decision-making.