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

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.

Identifying the Irrational Beliefs Hindering Your Decision Making

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] * I make it a habit to read and listen to everything published by entrepreneur and serial acquiror Brad Jacobs. He is the author of two best selling books, and has appeared on several of my own favorite podcasts, including Invest Like The Best hosted by Patrick O'Shaugnessy, and Founders hosted by David Senra. Brad has talked extensively about the personal and commercial importance of entrepreneurs keeping their minds healthy and clear. In his most recent book, he outlined a “toolkit” of sorts that he has leaned on for decades to help him do just this. The 5 tools in his toolkit included meditation, cognitive behavioral therapy, dialectical behavior therapy, positive psychology, and rational emotive behavior therapy ("REBT"). It was this last tool, REBT, that was largely unfamiliar to me, so naturally I bought a few books to learn more about it. Those books introduced me to a structured, highly logical, but ultimately very simple way to identify and challenge the hundreds of irrational beliefs and thoughts that present themselves to each of every day. I found the tool to be so compelling that I went searching for some of the world’s leading REBT experts. That search led me to Dr. Michael Bernard, a leading REBT practitioner, and entrepreneur and CEO himself. In our discussion today, we cover the basics of REBT, how to identify our own irrational beliefs, how to apply the tools of REBT to our daily lives, and the practical impacts of distorted thinking on our decision making at work.

"Great CEOs Are Lazy": Why the Best SMB Leaders Do Less—But Achieve More

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/landing-page/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/]⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * You’ve likely heard many times that CEOs should be spending more time working on their business than working in their business. While this idea makes good sense, just how realistic is it for a small business CEO, especially a new one? While we’d otherwise like to be spending our time mostly on strategy, culture, and capital allocation, being sucked into the day-to-day whirlwind feels like an inevitable part of small business leadership – or is it? My guest today, Dr. Jim Schleckser, is the author of a book entitled Great CEOs Are Lazy [https://amzn.to/4cFzN5T], and is also the founder of The CEO Project, where he and his team work with hundreds of CEOs of high growth companies. I think you’ll find that while Jim acknowledges that working in the business is an inevitable and acceptable part of a CEO’s role at times, you’ll also likely notice that Jim focuses a lot on leverage: That is, ways in which CEOs can generate the highest level of output through the fewest inputs, through things like purposeful hiring, delegation, and explicit rules around where to spend their time- and, importantly, where not to.

Are Search Funds Moving Up Market?

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] * Over the past few months, I’ve been presented with five separate opportunities that contemplated the acquisition of a company with $7M or more of EBITDA (this compares to the Search Fund average of $2.2M for the 2022-2023 cohort of Searchers). While I acknowledge that five data points don’t constitute a trend, at the very least this has piqued my curiosity. While the Search Fund ecosystem has worried – seemingly for over a decade now – about the possibility of middle-market Private Equity firms moving down market, it’s interesting to ask whether the inverse may now be happening, at least to a certain extent: Are Search Funds moving up market?