Podcast
Pain To Profits: Podcasts For Entrepreneurs
Hosted by Pain To Profits · EN
Join Samson Jagoras as he rolls up his sleeves and dives deep into the world of buying, building, financing, and investing in small and medium-sized enterprises (SMEs). As a serial entrepreneur and CEO of ClearlyAcquired.com, Samson brings experience in entrepreneurship through acquisition, marketing, branding, and creative strategies.This podcast is your front-row seat to insights and lessons from the trenches of Sleeves Up Equity Building.
12episodes
Episodes
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SBA Changes for Business Buyers: What You Need to Know | SOP 50. 10.8 SBA Changes (Effective June 1, 2025)
Jun 2900:14:33Tap to summarizeSBA SOP Changes: What They Mean for Search Funds, Buyers, and the Future of Main Street AcquisitionsAn AI-Generated Podcast from the Clearly Acquired Blog Briefing (May 2025)In this episode, we unpack the major policy shifts in the SBA’s latest Standard Operating Procedures (SOP 50 10 8 and SOP 50 10 7 Clarification), effective June 1, 2025—and explore how they impact search funds, deal structuring, and Main Street business acquisitions.This AI-generated episode is based on two Clearly Acquired articles: “Major SOP 50 10 8 SBA Changes” and “SBA’s New SOP Clarification”. We dive into the SBA’s intent to modernize and streamline business acquisition lending—while also examining the unintended consequences these changes may have on investor-backed entrepreneurship through acquisition (ETA).Key Takeaways:1. Big Wins for Borrowers:Personal Resource Test Eliminated: No longer disqualifies high-earners with liquidity. SBA will now consider “global cash flow,” including spousal income and rental earnings.Seller Notes as Equity: For the first time, seller notes can count toward the 10% equity injection—if placed on full standby for the life of the loan (max 50% of injection).CPA-Prepared Financials: When tax returns aren’t available, lenders can now accept CPA-reviewed statements—ideal for carve-outs, sole props, or new entities.2. Tougher Rules for Search Funds & Investors:Operator Must Have Control: SBA loans now require the buyer (searcher) to maintain day-to-day control and personally guarantee the loan. Any investor control—even informal or contractual—is prohibited.No Guaranteed Returns: Structures that prioritize investor repayment (e.g., redeemable preferred stock or waterfalls) are now disallowed. Investors must take true equity risk.Co-Borrower Requirements: All owners must sign as co-borrowers; sellers with retained equity under 20% must personally guarantee the loan for at least two years.3. Structural Shifts and Strategic Tradeoffs:Stock Purchase Mandated in Some Cases: If rollover equity is involved, the SBA will require stock deals—not asset purchases—reshaping tax and liability planning.Self-Funded Searchers Less Affected: Individuals using their own capital to search and raise deal-by-deal remain relatively untouched by these rules—but institutional models will need to adapt.Investor Support at Risk: Critics argue the SBA is misinterpreting the value investors bring (capital, mentorship, strategy), risking more failed deals and fewer exits for sellers.4. The Bigger Picture:Systemic Misalignment: Rising business valuations aren’t matched by SBA loan limit increases. Fewer deals pencil under the new framework, potentially creating a backlog of unsellable Main Street companies.Need for Nuance: Clearly Acquired advocates for balanced solutions—like milestone-based earnouts or protective provisions that don’t infringe on borrower control.5. Action Steps for Buyers & Advisors:Rethink deal structure early—especially if relying on investor capital.Ensure all equity is “true equity” with no disguised repayment guarantees.Leverage seller financing creatively within new limits.Build an expert advisory team to navigate compliance and maximize flexibility.Conclusion:While SOP 50 10 8 opens the door for more flexible, inclusive SBA-backed acquisitions, the clarified restrictions on investor control present challenges for traditional search funds. These changes could either streamline lending or choke off a generation of entrepreneurial dealmakers—depending on how the market adapts.This episode was generated using Clearly Acquired’s AI tools and is based on the company’s in-depth 2025 SBA SOP analysis. For the full articles, visit https://www.clearlyacquired.com/blog/major-sop-50-10-8-sba-changes-effective-june-1-2025----what-they-mean-for-business-buyers
Transcribe →From Search to CEO: The Entrepreneurial Acquisition Playbook
Jun 2900:24:06Tap to summarizeThe Ultimate Guide to Search Funds: Why Buying a Business Is the New StartupAn AI-Generated Podcast from Clearly Acquired's 2025 Guide to Search FundsIn this episode, we explore The Ultimate Guide to Search Funds (2025 Edition) by Clearly Acquired—a comprehensive briefing on how search funds are redefining the path to entrepreneurship, wealth creation, and legacy building.Search funds offer a compelling alternative to startups. Instead of building a business from scratch, aspiring entrepreneurs—called “searchers”—raise capital to acquire and operate existing, profitable businesses. These businesses, often valued between $5M and $50M, sit in the “missing middle”: too large for most individuals to buy outright, yet too small for traditional private equity. With baby boomer retirements creating an unprecedented transfer of business ownership, search funds are emerging as a strategic, scalable, and less risky path to ownership.We trace the evolution of the model—from Stanford MBA roots in the 1980s to today's tech-enabled, globally adopted, and increasingly diverse world of entrepreneurship through acquisition (ETA). The modern searcher is no longer just a freshly minted MBA but also includes mid-career professionals, seasoned operators, and industry experts seeking autonomy, control, and impact.Clearly Acquired is at the forefront of this movement. Their platform empowers searchers with proprietary deal-sourcing tools, real-time lender data, SBA loan brokerage, investor networks, educational playbooks, and coaching. Whether pursuing off-market opportunities or structuring complex capital stacks, Clearly Acquired supports buyers from first deal to final close—and even invests directly in promising operators through its Catalyst Fund.We also dive into the mechanics of deal structuring:Traditional vs. self-funded search fundsSBA 7(a) and 504 loans, seller notes, and revenue-based financingCreative equity structures and investor expectationsTools to balance risk, ownership, and upsideFor corporate professionals, search funds offer a powerful pivot—ownership without startup risk, equity with real upside, and the chance to preserve and grow established businesses that matter to communities. But the transition is not without challenges: mindset shifts, skill gaps, personal risk, and the need to build a solid team of advisors and capital partners.Finally, we compare search funds to other models like private equity and venture capital, showing how searchers uniquely combine lower risk, strong cash flow, and meaningful operator-led growth.Key Themes Covered:What search funds are—and why they’re growing fastThe evolution from MBA-only to globally accessible ETAHow Clearly Acquired supports searchers with capital, coaching, and techEquity and debt structures that power small business acquisitionsCorporate-to-ownership transitions and the skills requiredThe future of ETA and the legacy opportunityThis AI-generated podcast is based on Clearly Acquired’s 2025 Guide to Search Funds—created to help more entrepreneurs and investors understand and act on one of the most powerful trends in modern business ownership.Whether you’re exploring your first deal, raising capital, or advising others, this episode delivers a clear, actionable snapshot of the search fund ecosystem and how you can participate in the next wave of Main Street entrepreneurship.
Transcribe →Norvell Gives up $4.5M | Mindset of a Navy Seal | Google's Quantum Chip | SBA Loan Updates for Business Buyers
Dec 17, 202401:12:31Tap to summarizeNo description available
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MSM vs Elon, Juan Soto's a $765M Distraction, Kamala for "Person of The Year?"
Dec 11, 202400:58:48Tap to summarizeIn ep. 51, the guys discuss Axios & MSM joining forces vs Elon, why Juan Soto is a $765M distraction, Peter Schiff’s off-take on Bitcoin, Business Storytelling, Scientific Advertising, and a classic commercial from Purple. 00:34 - Axios & MSM Attack Elon Over The Truth 07:51 - Kamala Harris nominated for Person of The Year? 09:06 - Ray Dalio was right about the “Archestypical Big Cycle.” 10:22 - Juan Soto is a $765M distraction 23:03 - The guys ‘welcome’ Peter Schiff to the show 28:58 - How much equity should you get as an investor? 40:57 - Marc Randolph’s billion-dollar definition of success 44:28 - Dickie Bush breaks down Scientific Advertising 50:04 - Ameen Haque’s 5 Principles of Business Storytelling 56:56 - Purple’s classic commercial is hilarious
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Berkshire Hits $300B in Cash, The Digitalization of All Things, and GaryVee is Right About Live Shopping!
Dec 5, 202400:54:23Tap to summarizeIn ep. 50, the guys discuss the state of buyer confidence in the market, Berkshire sitting on $300B, the 'digitalization' of all things, and why GaryVee is right about live shopping on social. 0:00 - Episode recap 2:33 - Most Americans have no confidence to buy right now. 3:55 - Berkshire Hathaway’s cash position is now at $300B! 14:03 - Tom Bilyeu explains what focus looks like. 20:39 - Darius explores the thought that we are witnessing the ‘digitalization of all things.’ 34:48 - Classic footage from Bezos on why product is greater than marketing. 45:33 - GaryVee explains why live shopping on social is here to stay, but will anybody listen?
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Business lessons in College Football, side effects of the YCombinator era, & Jaguar vs Volvo
Nov 26, 202401:05:30Tap to summarizeIn ep. 49 of the pod, Darius and Samson discuss entrepreneurship through the lens of college football, the downside of the YCombinator era, Jersey Mike’s $8B sale, and close-out contrasting car makers Jaguar and Volvo. 01:29 - Samson’s entrepreneurial thoughts watching the CU Buffs this weekend 06:18 - Andrew D’Souza on the side effects of the YCominbator era of entrepreneurship 14:14 - Do billionaire operators ever stop feeling broke? 24:36 - Jersey Mike’s selling $8B with ONLY 3,000 locations. 33:31 - Every American owes $106,787…in theory. 34:56 - 700 regional banks are on the verge of failing 40:16 - A word from Trump’s New Treasury Secretary on America’s economic future 43:37 - The guys explore the Jaguar rebrand debacle with help from Newsweek and YouTube creator, Antonio 57:05 - The new Volvo ad makes the guys emotional
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MBAs Ruin Everything, Elon's Best Move, The Major Exec Sell-Off, & The Trump Shuffle Takes Over
Nov 20, 202400:59:23Tap to summarizeIn ep. 48 of the pod, Darius and Samson dig into why you shouldn’t hire MBAs, Elon’s boldest move in business, Rich execs are selling, The Trump Shuffle, and Volvo’s greatest ad ever! 0:00 - Intro 3:51 - Don’t hire MBAs 10:26 - Brian Armstrong on the chaos of startups 17:14 - Codie Sanchez on the power of one idea 20:07 - How Elon made the ultimate chess move 27:11 - Alex Friedman on creating your own reality 29:19 - The commodity basket & inflation are linked! 32:16 - Where is the big money going? Take a look. 37:58 - Steve Blank on The Art of The MVP 43:05 - Greg Isenberg with another must-read post 49:58 - The Trump Shuffle is taking over the country 54:35 - Dickie Bush on Volvo’s greatest ad of all time
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Trump Wins, Bitcoin ATH, Naval, Charlie Munger, and Must-See Content For Entrepreneurs
Nov 13, 202401:01:57Tap to summarizeOn ep. 47 of the pod, the guys dig into President-elect 47, Bitcoin ATH, The phase of the bull market we are in, Naval, Charlie Munger, how SaaS is evolving, and must-see content and ideas for your business. (Thumbnail: Chip Somodevilla/Getty Images) Episode Breakdown: 00:00 - Intro/Trump’s victory!! 00:50 - When you trust your team but they don’t trust you. 03:02 - Bitcoin resting at an all-time how. Are you in yet? 09:03 - We are in phase 3 of the bull market. Buckle up! 16:55 - Naval, a man on a mission to destroy wokeism. 23:18 - The Charlie Munger operating system for entrepreneurs. 30:52 - Greg Isenberg on the future of SaaS. 37:01 - How Spotify snatched billions of views at no cost. 46:43 - Marketing math that works for the next 10 years. 49:57 - The endless possibilities of creating content on social. 51:13 - Healthy businesses don’t obsess over metrics and goals. 57:08 - The post-election conversation we all need to have.
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25 More Basis Points, 90+ Sam Altman-isms, & Kamala Exploits the Black Church
Nov 6, 202400:52:27Tap to summarize00:00 - Intro & Check in 02:08 - The Fed cutting rates another 25 basis points 05:45 - Folks are waking up by way of their wallets 09:24 - The Market adjusted for inflation is shocking 18:02 - The US Government debt market collapse has started 25:00 - Interesting social content for entrepreneurs 27:30 - Sam Altman-ism for startup entrepreneurs 38:00 - Marketing wisdom from Rory Sutherland 45:23 - Is the Harris campaign exploiting the "Black Church?"
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Keynesian vs Austrian Economics, RIP Multifamily Real Estate, and Must Watch Social Content
Oct 29, 202400:59:50Tap to summarizePain Points co-hosts Darius Bell and Samson Jagoras survey the Keynesian vs. Austrian debate, multifamily crumbling, the most accurate recession predictor just went off, and the realities of buying a business from "SMB Attorney." We then jump into social content that surveys marketing and culture. Episode Rundown: 00:00 - Intro 01:01 - Keynesian vs Austrian Economics survey 19:01 - Multifamily delinquencies are up 990% 22:38 - The Sahm rule has been triggered. Look out! 27:07 - SMB Attorney drops knowledge for folks buying businesses 35:49 - The man who proved time was an illusion 42:41 - Our weekly content and culture showcase
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