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Business Builders And Buyers (ex-HoldCo Builders)
PrivateEquityGuy
140 episodes
3 hours ago
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, multiple expansion can’t be assumed, and real value creation matters more than spreadsheets. TI...
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Entrepreneurship
Business,
Investing
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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, multiple expansion can’t be assumed, and real value creation matters more than spreadsheets. TI...
Show more...
Entrepreneurship
Business,
Investing
Episodes (20/140)
Business Builders And Buyers (ex-HoldCo Builders)
How Smart Buyers Create Alpha Without Cheap Debt
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, multiple expansion can’t be assumed, and real value creation matters more than spreadsheets. TI...
Show more...
3 hours ago
25 minutes

Business Builders And Buyers (ex-HoldCo Builders)
The Playbook for 50-200% Annual Company Growth
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 structure scales. TIMESTAMPS 00:00 Deals are great, but the money is made in operations 02:15 The rea...
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4 days ago
48 minutes

Business Builders And Buyers (ex-HoldCo Builders)
I didn't join PE to be an operator
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” 3:38 No Real Path to Ownership 5:27 Where PE Talent Is Going Next Sponsors: https://capitalpad...
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1 week ago
9 minutes

Business Builders And Buyers (ex-HoldCo Builders)
There Is No Path — How Elite Investors Actually Build Their Lives, Careers, and Companies
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 a practical framework for building a career or business that actually compounds over decades. T...
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1 week ago
15 minutes

Business Builders And Buyers (ex-HoldCo Builders)
How I Quit My 6-Figure Job and Bought 9 Companies
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 3:00 Rolling up a beach town with chairs, linens, golf carts and a coffee shop 8:03 Buying a c...
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2 weeks ago
1 hour 7 minutes

Business Builders And Buyers (ex-HoldCo Builders)
How These Firms Turn $5M-15M Companies Into 100x Returns
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 returns 2:07 The simple playbook: buying small boring companies again and again 3:56 Engine #...
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2 weeks ago
24 minutes

Business Builders And Buyers (ex-HoldCo Builders)
From VC to Main Street: How AI Is Rewiring Service Businesses
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 now backing searchers at Shore Capital Partners. We dive into how AI is transforming traditional...
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2 weeks ago
51 minutes

Business Builders And Buyers (ex-HoldCo Builders)
How to Find 10x MOIC, 30%+ IRR Deals (Step-by-Step)
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 investors do differently to consistently catch those outliers. If you’re a searcher, investor, f...
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3 weeks ago
18 minutes

Business Builders And Buyers (ex-HoldCo Builders)
20 Acquisitions, 500 Investors, Zero Fund (The Private Equity Strategy No One Is Talking About)
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, over-capitalized balance sheets, manages messy founder transitions, and keeps hundreds of retail LP...
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4 weeks ago
1 hour 2 minutes

Business Builders And Buyers (ex-HoldCo Builders)
How I Retired at 30 as a Family Office Investor (Here Are the Investments I've Made)
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. TIMESTAMPS 0:00 Intro 1:43 Defining retirement: cost of living vs net worth 3:04 Immigrant upbringing ...
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1 month ago
1 hour

Business Builders And Buyers (ex-HoldCo Builders)
Buy 5 Companies as Fast as You Can (1-on-1 Advice From Fredrik Karlsson That Changed Everything)
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 its 63-year-old founder Fredrik Karlsson, the former CEO of Lifco - one of Sweden’s legendary se...
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1 month ago
11 minutes

Business Builders And Buyers (ex-HoldCo Builders)
Ian Rickwood on AI, Private Equity, Car Wash & Real Estate Investing | Henley Group
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 lesson on entrepreneurship and resilience 0:34 Who is Ian Rickwood and what is Henley Group? 1:04 The...
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1 month ago
58 minutes

Business Builders And Buyers (ex-HoldCo Builders)
How to Win Deals Over Private Equity (Even if They Pay 10-20% More)
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 0:00 The overlooked M&A superpower 4:55 Warren Buffett & Mrs. B: a deal built on trust...
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1 month ago
24 minutes

Business Builders And Buyers (ex-HoldCo Builders)
The Private Equity Bubble? | Inside a Private Equity Firm Built for What Comes Next
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, culture as an edge, off-market vs. banked processes, and the mindset required to win in the lower mi...
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1 month ago
59 minutes

Business Builders And Buyers (ex-HoldCo Builders)
The One System That Scaled from $3.5M to a 15-Company Portfolio (Sid Jashnani)
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; investors get standardized terms, governance, and distributions. If you are raising for a deal,...
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1 month ago
1 hour 11 minutes

Business Builders And Buyers (ex-HoldCo Builders)
7 Acquisitions Done — Buying Businesses on “Easy Mode” in 2025 (here’s why)
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 CapitalPad: https://capitalpad.com/ (HoldCo Builders is proudly sponsored by CapitalPad.) We c...
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1 month ago
33 minutes

Business Builders And Buyers (ex-HoldCo Builders)
How to Build a 7-Figure Company from Scratch (with Mac Lackey)
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… and guiding them to restructure and close for $42 million in cash just months later. Sponsors:...
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1 month ago
1 hour 4 minutes

Business Builders And Buyers (ex-HoldCo Builders)
How Builders Build Wealth That Lasts (and Mistakes to Avoid)
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-generation steward. Sponsor: This episode is sponsored by CapitalPad, the marketplace that connec...
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1 month ago
13 minutes

Business Builders And Buyers (ex-HoldCo Builders)
4 Portfolio Companies and The Gritty Playbook of Value Investing | Reggie Pryor Jr.
Value-driven investor and turnaround specialist Reggie Prior Jr. (Founder, Prior 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. Sponsors: This episode is sponsored by CapitalPad, the marketplace that connects acquisition entre...
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2 months ago
1 hour 3 minutes

Business Builders And Buyers (ex-HoldCo Builders)
How They Turned $8 Million into $450 Million (by Following THIS #1 SIMPLE Habit)
The greatest builders in history share one habit that changed their fortunes. You’ll hear how a single paragraph led Munger to a $500 million investment, how Jeff Bezos started Amazon because of one statistic in an article, and how Elon Musk saw an opportunity through the absence of information. This episode is about building your mental warehouse of ideas, training your intuition, and developing the kind of insight that compounds for life. The Sponsors This episode is brought to you by Ca...
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2 months ago
13 minutes

Business Builders And Buyers (ex-HoldCo Builders)
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, multiple expansion can’t be assumed, and real value creation matters more than spreadsheets. TI...