When Both Sides Are Right: Navigating the Trade-Offs That Define Leadership

When Both Sides Are Right: Navigating the Trade-Offs That Define Leadership

This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://boulaygroup.com/services/search-funds/] * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://oberle-risk.com/in-the-trenches/]     * This episode is brought to you by ⁠⁠Kilpatrick, a leading global law firm with a dedicated search fund team that works with searchers from inception, to acquisition, to exit⁠⁠ [https://ktslaw.com/Services/BusinessFinance/Entrepreneurship-Through-Acquisition-Search-Funds]. * ⁠⁠⁠⁠⁠Click Here to Subscribe to the In The Trenches YouTube Channel⁠⁠⁠⁠⁠ [https://www.youtube.com/@InTheTrenchesSMBPodcast] * Link to a related blog post: How to Know When it’s Time to Stop [https://mineolasearchpartners.com/2022/08/18/how-i-made-my-decision-to-step-down-as-ceo/] * One of the most challenging aspects of leadership is navigating the seemingly endless collection of tensions and trade-offs that exist within any organization. These situations are difficult precisely because they rarely involve a choice between something that is clearly right and something that is clearly wrong. More often, leaders find themselves choosing between two priorities that are both important, both defensible, and both worthy of attention. In these situations, not only must leaders determine where to allocate resources, but they must also manage the internal tensions that frequently emerge when different people, teams, or departments become closely aligned with one side of the trade-off or the other. Throughout my tenure as a CEO, I repeatedly encountered situations like these. This week, we explore seven specific examples of these leadership trade-offs, and why I believe they are among the most difficult decisions that leaders are asked to make.

The Wisdom of Failure: Growing from our Personal and Professional Setbacks

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://oberle-risk.com/in-the-trenches/]     * This episode is brought to you by ⁠Kilpatrick, a leading global law firm with a dedicated search fund team that works with searchers from inception, to acquisition, to exit⁠ [https://ktslaw.com/Services/BusinessFinance/Entrepreneurship-Through-Acquisition-Search-Funds]. * This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://boulaygroup.com/services/search-funds/] * ⁠⁠⁠⁠Click Here to Subscribe to the In The Trenches YouTube Channel⁠⁠⁠⁠ [https://www.youtube.com/@InTheTrenchesSMBPodcast] * Today’s episode is all about failure – I know that doesn’t sound like a particularly sunny way to begin an episode, but stick with me. My guest today, Dr. Larry Weinzimmer, argues that failure is not just an inevitability in business and leadership — it is often the primary source of meaningful growth and long-term success. Importantly, he argues that this is true at both a personal and organization level. In our conversation today we discuss how those who are achievement oriented often have a hard time digesting this reality, how bosses and Boards of Directors can create environments where failure is tolerated but not necessarily actively encouraged, the role that egos tend to play in organizational failures, what a good post-mortem and pre-mortem sounds like, what “learning” from a failure actually looks like at a highly tactical level, why success can breed over-confidence and blind spots (including how to spot common warning signs in advance), and how to balance the importance of persistence with the wisdom of knowing when it’s time to make a change.

The Real Reason Why Most Companies Miss Their Annual Goals

This episode is brought to you by Kilpatrick, a leading global law firm with a dedicated search fund team that works with searchers from inception, to acquisition, to exit [https://ktslaw.com/Services/BusinessFinance/Entrepreneurship-Through-Acquisition-Search-Funds]. * This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://boulaygroup.com/services/search-funds/] * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://oberle-risk.com/in-the-trenches/]     *   ⁠⁠⁠Click Here to Subscribe to the In The Trenches YouTube Channel⁠⁠⁠ [https://www.youtube.com/@InTheTrenchesSMBPodcast] * There’s a well-known maxim that states “Strategy without execution is hallucination”, and in today’s episode I’ll share with you why I think that’s true. I’ll do so by sharing some of the lessons that I learned as a CEO related to executing on the strategy that I set at the beginning of each year. In my experience, strategy is actually the easy part: Almost any mediocre CEO can set logical and compelling goals for a company, but it’s the truly skilled CEO who adjusts her tools, systems and processes to regularly and successfully execute on those same goals.  As Jim Collins and Jerry Porras (authors of Built to Last) rightly said: “Building a visionary company requires one percent vision and 99 percent alignment.” Today, I’ll share with you the best tools that I’m aware of to create that very alignment.

Ten Ways to Underwrite a Conservative and Realistic Base Case

This episode is brought to you by⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://boulaygroup.com/services/search-funds/] * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://oberle-risk.com/in-the-trenches/]     *   ⁠⁠Click Here to Subscribe to the In The Trenches YouTube Channel⁠⁠ [https://www.youtube.com/@InTheTrenchesSMBPodcast] * When building a model and underwriting an acquisition more broadly, many prospective acquirors understandably struggle with how to balance calculated optimism about the future on one hand, with a sense of what is realistically achievable on the other. While investing is an inherently optimistic act (after all, you wouldn’t make the investment if you didn’t believe that the future was likely to be better than the present), acquirors must balance that optimism against the company’s historical performance, possible future headwinds outside of their control, and execution challenges common to first-time CEOs, among other considerations. In today's episode, I present prospective acquirors with ten different ideas on how to underwrite a conservative and realistic base case.

Hiring Your Second in Command: With Cameron Herold, Founder of the COO Alliance and Former COO of 1-800-GOT-JUNK

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://oberle-risk.com/in-the-trenches/]     * This episode is brought to you by⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://boulaygroup.com/services/search-funds/] * ⁠⁠Click Here to Subscribe to the In The Trenches YouTube Channel⁠⁠ [https://www.youtube.com/@InTheTrenchesSMBPodcast] * A “second-in-command” (sometimes a Chief of Staff, sometimes a Chief Operating Officer, and at other times a different title entirely) can be among a CEO’s more important and impactful hires. But, in my experience anyways, there is a lot that we don’t really understand about this hire: How do you know that you’re ready to hire one? What should they do and what should they not do? What title should we give them (and do titles even matter)? How much do we pay them and what forms of compensation are most appropriate? Should individual entrepreneurs consider hiring one as a sort of “proxy” for a business partner? To help me answer all of these questions (and a few more), I could think of no better guest than Cameron Herold. Among many other accolades, Cameron is the former COO of 1-800-GOT-JUNK (which he helped to grow from $2M to $106M in revenue during his 6 year tenure as COO), Founder of the COO Alliance (a peer network for “second in command” professionals, similar EO or YPO for Chief Executives), host of the “Second in Command” podcast, and author of a book of the same name. Based on all of these experiences, Cameron is now a highly sought after coach and speaker, particularly within the SMB community.