Search Fund CEO: I skipped the startup grind, bought a company and made myself CEO

Jackson is CEO of Passmark Software, a 27 year old company he acquired through what's known as a traditional search fund model. He raised capital from 18 investors, reached out to 2,500 business owners, had conversations with about 100, went deeper with 20, and ultimately bought a business he now leads. He didn't have a technical background. He didn't start the company. He’s proof that the path exists for others who want to do the same. In this conversation, Jackson shares what it actually takes to buy a business when you don't have one yet, how he raised capital from investors who were backing him and not a business, why most business owners don't know what their company is worth, and what he's learned now that he's sitting in the chair he worked years to get to. He also opens up about the nine month transaction process, the due diligence that nearly derailed the deal, and the moment he realized his investor pipeline had dried up and he had to find a completely different way to reach people. He explains: - What a traditional search fund is, and why it's a third path to the top that most people never consider - How he raised capital from 18 investors before he had a business, and why that took nine months - Why he contacted 2,500 business owners, and what the most common reasons were that deals didn't proceed - The questions he asks to filter out businesses that can't survive without the owner - Why most founders don't know what their business is worth, and how that creates friction in negotiations - What business owners should do three to five years before they want to sell to maximize their exit value - The moment his investor pipeline dried up, and the analog strategy he used to unlock a hidden capital market - Why handwritten letters to investors' homes opened more doors than any automated outreach ever could - How he leads a technical team when his expertise is in sales and commercial strategy, not software engineering - What no amount of due diligence can prepare you for when you finally step into the CEO seat - Why 500,000 Australian businesses have no succession plan, and what that means for the next generation of business leaders If you've ever wondered whether there's another way to lead a business without starting from scratch or waiting decades to climb the ladder, this episode will show you the path that most people don't know exists. Timestamps: ### Chapters - **00:00:00** Introduction - **00:02:00** The Search Fund Model: A Third Path to the Top - **00:06:46** What Search Funds Bring That Startups Don't - **00:10:42** Contacting 2,500 Businesses: What Makes Deals Fall Apart - **00:14:05** The Owner Dependency Problem: When Founders Can't Step Away - **00:16:44** Valuation Gaps: When Owners Overestimate Their Business Worth - **00:19:20** Preparing Your Business for Sale: The Three-Year Plan - **00:22:49** Raising Capital from 18 Investors: The Nine-Month Journey - **00:27:38** The Belief That Anything Is Possible - **00:30:18** The Handwritten Letter Strategy: Finding Hidden Investors - **00:38:25** Deal Signed: The Relief of Closing After Nine Months - **00:41:33** The First 60 Days: Customer Conversations and Learning the Business - **00:42:03** Leading Without Technical Expertise: Running a Tech Company as a Commercial Leader - **00:50:02** What Due Diligence Can't Show You: Market Disruption and AI Search - **00:51:24** The 500,000 Business Succession Crisis: Opportunity and Risk - **00:53:55** Getting Started: Books, Resources, and the Search Fund Community We're just getting started! Subscribe for more conversations with founders, operators, and their advisers. Jackson Allan: LinkedIn https://www.linkedin.com/in/jacksonallan1/ Passmark Software https://www.passmark.com/ At The Top Youtube: https://www.youtube.com/@atthetopwithben Instagram: https://www.instagram.com/atthetopwithben/ LinkedIn: https://www.linkedin.com/company/at-the-top-with-ben/ Spotify: http://open.spotify.com/show/1GTjCXqdQzQtZ33idMpQgo?si=C5gNvXDZSkWdxBz-mW13AA Apple Podcasts: http://podcasts.apple.com/us/podcast/at-the-top/id1893782299