Buyers and Builders

This episode breaks down how Jeremy Giffon ( https://x.com/jeremygiffon ) thinks about special situations, forced sellers, and overlooked businesses, showing why the best investments come from understanding incentives, human behavior, and coordination problems rather than complex models or market timing. Show notes: 0:00 Special situations in the lower middle market 6:18 The perfect business is ge...

Mike Markus ( ⁠https://x.com/PrivatEquityGuy ) talks to Jeremy Yamaguchi ( https://x.com/jeremyyamaguchi ) about how he acquired 10 companies in 18 months. Show notes: 0:00 How Jeremy built and exited 3 home services businesses 5:48 Why “boring” home services were a massive tech opportunity 8:11 Why he chose venture for Lawn Love + the YC story 12:41 Why home services are still wildly fragmented a...

This one hire is something all profitable, cash-flowing traditional businesses can do. Yes, it can be a significant investment -- great specialists aren’t cheap -- but in the right setup, it can completely change the trajectory of a company. I share two real-world examples of owner-operated, non-glamorous businesses that hired a Chief Investment Officer to professionally manage excess cash. In bot...

In this episode, Todd Saunders shares how one small group of customers with much better retention changed the direction of his entire business. Instead of chasing trends or going broader, he went deep into a simple, overlooked niche -- independent flooring retailers -- and ended up building the core software used across the industry. Todd explains why brand and community mattered more than feature...

We go deep on Justin Ishbia, co-founder and Managing Partner of Shore Capital Partners - one of the most successful lower-middle-market private equity firms in the U.S. After inviting Justin on the podcast and being asked to reconnect in early 2026, I used the time to study Shore’s work more closely. This episode is the result: a synthesis of Justin’s long-form interviews, public commentary, and S...

Steve Lawrence, the founder of Uncomplicated Group went from middle management at a $14B manufacturer to buying five businesses in a few short years -- now running two injection-molding factories, employing 45 people, and shipping 200M parts a year. But this episode isn’t about the highlight reel. It’s about the real path: quitting his job for a deal that collapsed at the finish line, burning cash...

For the last 20 years, private equity followed a simple formula: buy with leverage, cut costs, rely on multiple expansion, exit at a higher valuation. That playbook worked incredibly well. But it no longer does. In this episode, I break down why the old private equity model is structurally broken - not just cyclically - and why a new model is emerging. A model where cheap debt doesn’t save you, mu...

In this episode, I’m joined by John Seiffer - the person investors, company buyers and operators call when growth starts getting expensive, messy, or fragile. John has spent decades across manufacturing, software, restaurants, chemicals, and professional services, and he sees the same pattern over and over: founders are great at the product and the sale… but the company can’t scale until the struc...

The future of private equity talent is moving toward ownership. We explore why the traditional PE career path is breaking, why carry no longer delivers the upside it once promised, and why more professionals are choosing to build - not wait - for real equity. You will discover: 0:00 The Quiet Exodus Inside Private Equity 1:45 Carry That Never Materializes 2:56 “I Didn’t Join PE to Be an Operator”...

In this episode, we break down a powerful idea from Jeffrey Walker, a private equity veteran who backed thousands of entrepreneurs and watched success and failure up close. His conclusion is uncomfortable but freeing: the people who win don’t follow a path, they create one. You’ll hear why talent is overrated, why “perfect careers” quietly fail, how one pathless founder built a $200M company, and...

Today’s guest, David Dowda (Dowda Holdings), went from burned-out insurance salesman working 80-100 hour weeks to buying his first business doing just $30,000 a year - fully seller-financed. Ten years later, he owns nine companies across multiple industries - all acquired with zero outside equity and often minimal cash down. TIMESTAMPS 0:00 How he bought a $30k revenue business with zero cash down...

How these serial acquirers generate 20-40% annual returns for decades? They buy small, niche, profitable companies again and again. In this episode, we break down the strategy, the structure, and what private buyers can learn from the greatest acquisition machines on earth. TIMESTAMPS 0:00 Why tiny acquisitions beat big deals 1:12 21x, 120x, 375x: Lifco, Addtech, Constellation & Heico’s insane...

In this episode, Cyrus Hessabi from Shore Capital Partners breaks down what it really looks like to build AI-enabled services, transition from VC to micro-cap private equity, and back searchers buying “boring” but powerful businesses. Cyrus has lived every chapter of the operator-investor journey: aerospace engineering, Salesforce sales, venture capital, architecting AI rollups at OpenOcean, and n...

Most people in ETA quote the Stanford Search Fund Study, but almost no one looks at what investors actually earn. In this episode, we break down new Yale data from 1,192 investor-level outcomes and shows why access, not modeling, is the #1 driver of 10x MOIC, 30%+ IRR results. You’ll learn why your portfolio will never be “the index”, how a tiny % of deals drive almost all returns, and what elite...

Sequoya Borgman has quietly built one of the most interesting retail-funded private equity machines in America. Since launching Borgman Capital in 2017, he’s acquired 20 companies across 8 platforms and raised deal-by-deal from 500+ individual investors instead of institutions. In this episode, we break down how he sources mostly off-market deals in second-tier cities, structures conservative, ove...

Akshay Ramachandran is a retired family office investor. In his last role, Akshay was the sole analyst at a New York-based single family office, reporting directly to the portfolio manager. Together they analyzed over 60 industries using a simple strategy: buy and hold great businesses run by great management teams. In this episode, he explains his biggest winner and covers the whole story. TIMEST...

There’s a holding company that almost no one talks about, yet it might be one of the most efficient compounding engines. RÖKO owns 29 niche, traditional businesses, runs 21% margins, generates 14.5% returns on capital and keeps acquiring new companies every quarter. And they do all of this with a headquarters team of just eight people. In this episode, I break down the full story behind RÖKO and i...

Ian Rickwood, Founder and CEO of Henley Group, has quietly deployed $4B+ across US and Europe, built and sold food chains, and is now rolling up US car washes using AI-driven site selection. We also dive into what great operator partners look like, how to handle bad deals, and what it’s really like to build a serious firm with your spouse and kids. TIMESTAMPS: 0:00 “Don’t give up” Ian’s core lesso...

One of the most underrated skills in business acquisitions. Beyond financial models and deal structures, many great acquisitions happen because buyers know how to connect with sellers on a human level. #BusinessAcquisitions #DueDiligence #MergersAndAcquisitions #HoldCoBuilders #ListeningSkills #DealMaking #EntrepreneurshipThroughAcquisition #PrivateEquity #BusinessBuying #SMBacquisition TIMESTAMPS...

My guest today is Joel Mathew, Head of Originations at Woodson Equity. We discuss how his entrepreneurial path led him into private equity, Woodson’s “inch wide, mile deep” focus on diversified industrials and business services, and why they favor hands-on, control deals. Joel shares a live carve-out playbook, how he sources more than a 1,000 deals a year, the first-100-days operating cadence, cul...

How Sid Jashnani scaled his firm into a portfolio of 15 companies and $77 million in revenue. If you’re an investor or builder, this is a masterclass in turning chaos into compounding cash flows. Sponsors: This episode is sponsored by CapitalPad, the marketplace that connects acquisition entrepreneurs with investors who want exposure to small-business deals. Operators list live deals in one place;...

Buying a small business and raising the equity shouldn’t take a roadshow. In this episode, Donza Worden (ex–institutional PE, Clear Peak Capital) and Travis Jamison (multi-exit founder turned investor) break down how CapitalPad makes both sides easier: 1) curated deal flow for accredited investors; 2) and a streamlined path to capital for independent sponsors/searchers. Start deploying today with...

My guest today is Mac Lackey, an entrepreneur who has founded and sold six companies, each with 7-and 8-figure exits - including two back-to-back internet businesses during the dot-com boom. In this episode, Mac breaks down the exact mindset and playbook that helped him turn businesses into life-changing exits. He shares the story of advising one company who was struggling to sell for $25 million…...

You’ve spent years building something from nothing — finding deals, operating, and growing real value. But what happens after success? Once liquidity arrives, how do you protect your wealth, make it work for you, and ensure it endures for generations? In this episode, we explore the mindset and structure behind lasting wealth — the difference between being a first-generation builder and a third-ge...

Value-driven investor and turnaround specialist Reggie Pryor Jr. (Founder, Pryor LLC) breaks down his simple but relentless playbook: buy what others overlook and rebuild it into a durable cash flow machine. We go from his first mentor (textile legend Jimmy Gibbs) to reading Graham & Dodd, using collateral to get started, and why he rarely sells, preferring to borrow against assets instead. Sp...