A Cybersecurity Survival Guide for Small Businesses

A Cybersecurity Survival Guide for Small Businesses

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] * * Download your free copy of Kip's Book, Fire Doesn’t Innovate [https://cr-map.com/in-the-trenches/] * In 2026, you probably don’t need to look terribly far to read about both the frequency and seriousness of cyber attacks on both individuals and small businesses. Because of how unfortunately common these attacks have become, and because of how difficult they can be to understand if not explained at an appropriate level of detail, I thought it would be worthwhile to dedicate an entire episode to discussing “Cybersecurity 101" for Small Businesses. To help me, I was joined by Kip Boyle, a security expert with 25 years of experience in cybersecurity and IT risk management for organizations in insurance, financial services, technology, military, and logistics, among others. Prior to his current role as a consultant and fractional chief information security officer for small businesses, Kip spent many years as the Chief Information Security Officer at PEMCO Insurance and has also served as the Chief Security Officer of a transaction processing business, and an IT services provider to financial institutions.

A Glimpse Into The First 90 Days as a New CEO

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] * You probably don’t need to have much of an imagination to envision just how intimidating it can be to be a first-time CEO within your first 90 days. I remember my own such experience like it was yesterday, and still remember it as a time in my life where I was, paradoxically, both excited and insecure, confident and fearful, relieved and anxious, tired and energized. How to approach the first 90 days as a new CEO, including what to do and what not to do, is also among the most frequently asked questions that I’ve received over the past 14 years. For this reason, I thought it would be a great idea to interview 3 CEOs, each at different stages of their leadership journeys, and ask each of them the same 3 questions: 1. Their general approach to the first 30 days 2. What worked 3. What didn’t work I think you’ll find their answers to be highly instructive, particularly the themes that seemed to be consistent across all 3 of their stories. Today I was joined by John O’Brien, CEO of Echo Point Books & Media, Matt Fiedelholtz, co-CEO of Stage 2 Data, and Ethan Walz, co-CEO of Allied Electric. Please enjoy!

The Most Meaningful Lesson that I've Learned Over the Past 12 Months

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] * Regular listeners of the show will know that I often conclude with the same question: “What is the most meaningful lesson that you have learned over the past 12 months, across any domain of your life?”. I’ve received so many interesting answers to this question that I decided to compile them into a single episode, that features the answers of 15 of our previous guests. One of my favorite quotes is “we need to be reminded more than we need to be taught”, which suggests that many of our most meaningful lessons are ones that we already know at some level, but often need to experience to fully appreciate their importance. What I loved most about today’s episode is not just how simple and fundamental the answers were, but also how they spanned so many different domains of life: Business, personal, family, and spiritual, just to name a few.

A Peek Behind the Curtain: What Small Business Ownership *Really* Looks Like

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] * Since the first blog post that I wrote in April of 2021, I have been rather public with my opinion that nobody knows what it’s like to be an entrepreneur or CEO unless you’ve been one. Personally, and professionally, we face both challenges and opportunities that few others can relate to. Though many understand the rewards of company leadership (things like compensation, decision making authority, and independence) few understand the sometimes-arduous journey that’s required to both get there, and to stay there. This is why it can feel genuinely lonely at the top: In spite of their best efforts, our spouses, direct reports, and friends simply don’t understand what it’s really like. More accurately, they can’t be expected to. The point of today’s episode is to give the uninitiated a peak behind the curtains, and to provide but one example of what leadership really looks like at the ground level. My guest today, Rishi Sahel, is a great example of a CEO who has withstood more than his share of punches to the gut: As you’ll hear in our discussion today, these punches included (but were not limited to) an acquisition of a manufacturing company in the middle of Covid when lockdown orders were in full effect, a post-covid supply chain crisis, Post-covid runaway inflation, a Lost warehouse, an attempt to buy their primary manufacturing facility from out underneath them, wire fraud, tariffs impacting a global supply chain and global customer base, and one unforgettable presentation to members of a local city council – all of which is about a million miles away from the comfortable confines of Bain, where Rishi spent many years prior to pursuing his dream of acquiring a small business. As you’ll hear, despite all of these challenges, the company that he has built has enjoyed incredible growth and success. But hopefully better understanding the details of his journey will give you pause the next time you’re tempted to get too enamoured with what seems to be an unambiguously positive headline. In presenting Rishi’s story to you, I don’t at all mean to suggest that leadership is all downside and no upside. Quite the contrary, in fact. Instead, I’m providing you with this dose of reality only because I assume you’re much more familiar with the upsides of entrepreneurship and leadership, and much less familiar with the price that you’re likely to have to pay in order to receive those benefits.

$2B Company Founder on Youth, Inexperience, and Why You're More Ready Than You Think

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] * My guest today is Ronnen Harary, the Co-Founder and Chairman of Spin Master Toys, the fourth-largest toy company in the world behind only Lego, Mattel, and Hasbro. Alongside his business partners, Ronnen co-founded Spin Master in 1994 and eventually transformed it from a three-person startup into a publicly traded company with a market capitalization of ~$2B, generating ~$2.3B in annual revenue. In our conversation today, we talk about the four major themes that stuck out to me from Ronnen’s career: 1. Youth, inexperience and how that frames how we ought to think about taking risk in our lives and careers 2. Tail events: The impact of a small number of outcomes that generate a disproportionate share of results 3. Relationships between business partners: How he thinks about what makes for a great partnership (and what makes for a bad one) 4. Once you've accomplished your wildest dreams, what happens to your relationship with risk and ambition?