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HoldCo Builders
PrivatEquityGuy
129 episodes
3 days ago
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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Entrepreneurship
Business,
Investing
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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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Entrepreneurship
Business,
Investing
Episodes (20/129)
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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2 days ago
58 minutes

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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4 days ago
24 minutes

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 week ago
59 minutes

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 week ago
1 hour 11 minutes

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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2 weeks ago
33 minutes

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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2 weeks ago
1 hour 4 minutes

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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3 weeks ago
13 minutes

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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3 weeks ago
1 hour 3 minutes

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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4 weeks ago
13 minutes

HoldCo Builders
How to Build Proprietary Deal Flow? (15 Off-Market Acquisitions)
Peter Lang has done 22 acquisitions (mostly off-market). Grant spent a full day at his masterclass—and it was the most valuable single-day M&A professional development he has ever had. Most people share 101-level fluff; Peter was selective about who he let in the room, so he went straight to 202/303-level tactics: - a 128-question pre-LOI audit, - “pre-diligence,” - risk registers, - and first-call bonding that actually wins deals. During the session he even had them cold DM a business ...
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1 month ago
29 minutes

HoldCo Builders
Lessons from 100+ Acquisitions You Can Implement TODAY | Joe Liemandt
In this deep dive, we unpack the operating philosophy of Joe Liemandt - builder of Trilogy Software and ESW Capital, and now the force behind Alpha School - including lessons from 100+ acquisitions. Liemandt became a billionaire by buying sleepy software assets and turning them into cash machines, vanished from public view for years, then re-emerged with a mission to rebuild systems from first principles. This episode isn’t about education - it’s about how great operators think. The Sponsor ...
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1 month ago
28 minutes

HoldCo Builders
How We Bought 27+ Businesses and Built a $1 Billion HoldCo at 39 | Steve Carroll Interview
Steve Carroll is the CEO & co-founder of Kelso Industries, a national MEP services platform uniting HVAC, mechanical, plumbing, and electrical companies. In just a few years, Kelso went from a gritty, nearly-broke first acquisition to 29 acquisitions and $1B+ in revenue. Steve breaks down the bruises and the blueprint: why their first year almost killed the business (including a single job that wiped out a year of profit), the switch from “buy and replace” to a partner-and-keep-the-owner...
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1 month ago
1 hour 10 minutes

HoldCo Builders
How I Completed 12+ Acquisitions and Still Built a New Roll-Up
My guest today is Nick Hatchka, founder of Cube Investments, which has completed over a dozen acquisitions. Nick is now building a regional platform of generator dealers and service businesses in California alongside his operating partner, Dylan Ferguson. We discuss his journey: - to independent sponsorship, - lessons from 12+ acquisitions, - what makes a good business model, - partnering with operators, - and buying seller-dependent companies. Sponsors This episode is brought to you by Cap...
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1 month ago
52 minutes

HoldCo Builders
How to Raise $450 Million at 31 with No Track Record (and Do 90+ Deals) | Urs Wietlisbach Research
Imagine being in your early 30s, launching a private equity fund, and raising $450 million for your first fund. (No track record. No rich father or uncle.) Urs Wietlisbach, one of the three co-founders, led client relationships and fundraising, pushed proactive deal sourcing and thematic research, and kept the team focused on pensioners as the ultimate client. Sponsors This episode is brought to you by CapitalPad — a marketplace that connects acquisition entrepreneurs who need capital with ...
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1 month ago
25 minutes

HoldCo Builders
9 Figure Exit How I Built and Sold to Private Equity (Alexis Sikorsky Interview)
My guest today is Alexis Sikorsky. An entrepreneur who bootstrapped, scaled, and ultimately sold a company in a 9-figure exit. Sponsors This episode is brought to you by CapitalPad — a marketplace that connects acquisition entrepreneurs who need capital with investors who want exposure to small-business deals. Standardized terms, governance, and distributions included. If you’re raising for a deal—or want to back operators—check out https://capitalpad.com/ ETA Europe — sharp weekly curation...
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1 month ago
1 hour 18 minutes

HoldCo Builders
He Bought 4 Small Businesses with ZERO Finance Experience (Nikolai Dimitrov Interview)
Nikolai Dimitrov went from pro football to building Unity Investment Partnership, where he buys small, reliable, everyday businesses, paying 3–4× cash flow with seller-aligned structures, and has closed 4 acquisitions so far. We cover his rocky start (including a Facebook group against him), four acquisitions, why “terms more important than price,” post-acquisition reporting, incentives, and how culture and a real CEO will power Unity’s next stage. CapitalPad: the SMB investment platform fo...
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1 month ago
40 minutes

HoldCo Builders
I Raised $11.7M To Back 13 Self-Funded Searchers | Grant Hensel Interview
Grant Hensel has started 10 companies (7 failed, 2 sold, 1 scaled), bought a business his wife now operates, and then got obsessed with backing self-funded searchers. He’s the founder of Entrepreneurial Capital, raising ~$11M to invest in “cockroach” SMBs at 3–5x earnings alongside gritty owner-operators. If you’re buying or backing boring, profitable businesses, this is a playbook episode. CapitalPad: the SMB investment platform for accredited investors & searchers. Join now: https://c...
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1 month ago
51 minutes

HoldCo Builders
60+ Search Fund Investments: What Industries Excite Him The Most TODAY
A deep-dive on the operator-first path to buying a small business. Told through the lessons of investor-turned-operator Tim Ludwig (60+ portfolio companies; now co-runs Majority Search). Learn how search funds actually work, which industries to invest in, which searchers to back, why EQ beats IQ in a first-time CEO, and the exact playbook from LOI → close → the first 100 days. Want a newsletter that builds trust—but have zero time? Spacebar Studios handles strategy, writing, design, and dis...
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2 months ago
27 minutes

HoldCo Builders
How I Left PE, Bought 2 SaaS Businesses (Raising a Fund Next?) | Donza Worden Interview
Former institutional investor Donza Worden (co-founder, Clear Peak Capital) breaks down why many private equity pros aren’t truly investors—and what he’s doing differently as an independent sponsor who closed two platforms in year one (IT services & vertical SaaS). Sponsored by CapitalPad—deal flow for serious investors. Built by world-class engineers and PE operators. Apply here: https://capitalpad.com/ This episode is also sponsored by Space Bar Studios. If you’re an investor, holdco,...
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2 months ago
37 minutes

HoldCo Builders
This 70/30 Model Leads to Highest Returns
I spoke with an operator who sold his own company - then turned around and bought eight more. His playbook is specific, bank-friendly, and built for growth. In this episode, I’m unpacking the lessons from those deals: 00:00 Intro: From exit to 8 acquisitions 00:26 Portfolio averagE: 4.7x paid; $4.1M EBITDA 00:52 Structure banks love: 70% now, 30% later; owner reinvests 01:18 Growth thesis: target 5x MOIC + “second bite” bigger than first 03:30 Value creation: capital allocation, incentives, ...
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2 months ago
6 minutes

HoldCo Builders
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...