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HoldCo Builders

PrivateEquityGuy

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The HoldCo Builders with PrivateEquityGuy is a place where you can find meaningful conversations about holding companies, buying and building businesses, entrepreneurship, investing, and more. Be sure to follow the podcast, so you never miss an episode!
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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 emerg…
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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…
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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 Mater…
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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, ho…
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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 …
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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: …
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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 ca…
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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 % …
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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 i…
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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…
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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 epis…
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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.…
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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 #Privat…
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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…
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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-busin…
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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 independe…
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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 c…
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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 betwe…
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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, p…
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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 …
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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, - …
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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-emerge…
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My guest today is Nick Hatchka, founder of Cub 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 m…
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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 ulti…
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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 di…
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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,”…
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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, profita…
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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 …
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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 engine…
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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% l…
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Co-invest in curated SMB acquisitions led by proven searchers and independent sponsors. Get a full deal room with financials, tax returns, sponsor profiles, and value-creation plans. No management fees; CapitalPad participates only after investors get their capital back and profits are earned. Operators under LOI can also use CapitalPad to fill equ…
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At 42, Sam Turner had the title, the pay, the lake view in Switzerland — but he was not happy. So he engineered his exit, just as COVID nuked his industry. Instead of crawling back, he jumped into buying gritty local businesses. His first deal nearly sank him — wrong sector, thin margins, the people piece ignored. Most would quit. Sam doubled down,…
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What happens when a holding company thinks like an immigrant, moves like an entrepreneur, and plays the long game with permanent capital? In this episode, we unpack the operating system of Fernando De Leon and Leon Capital Group—a family holding company that conceives, develops, owns, and operates businesses across real estate, financial services, …
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Want to grow your B2B business? Start with your inbox. Spacebar Studios builds newsletters that drive pipeline, build authority, and generate real revenue. Bonus: The first six founders who raise their hand get their newsletter built for free. Reserve your slot: https://www.spacebarstudios.co/inquire Scalepath is the sponsor of this episode. If you…
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Rand Larson helps small business owners beat the loneliness of operating by building tight, ROI-driven peer groups. We dig into what actually works: working-capital traps, hiring/firing discipline, burnout, and why some owners sell just 12–24 months post-close. Scale Path is the sponsor of this episode. If you’re a searcher or operator and want rea…
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Want to build a media asset your competitors can’t copy? Spacebar Studios turns B2B newsletters into profit centers — driving pipeline, authority, and long-term enterprise value. - 115k+ subscribers in compliance - 7-figure ARR driven by email - Built for SaaS, services, and niche B2B markets First 6 founders this month get their newsletters launch…
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Your newsletter is the gallery. Gagosian sold because his collectors heard from him—constantly. Spacebar Studios builds the newsletter that keeps you in front of founders, LPs, and operators every week. Book a call to get yours (First 6 founders get theirs launched for free): https://www.spacebarstudios.co/inquire Default aggressive—together. Larry…
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Want to build a media asset your competitors can’t copy? Spacebar Studios turns B2B newsletters into profit centers — driving pipeline, authority, and long-term enterprise value. - 115k+ subscribers in compliance - 7-figure ARR driven by email - Built for SaaS, services, and niche B2B markets First 6 founders this month get theirs launched for free…
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Want to grow your B2B business? Start with your inbox. Spacebar Studios builds B2B newsletters that drive pipeline, build authority, and generate real revenue. - 115k+ subs in compliance - 7-figure ARR from email First 6 founders get theirs built free Reserve your slot here: https://www.spacebarstudios.co/inquire Running a business can feel like yo…
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Want to grow your B2B business? Start with your inbox. Spacebar Studios builds B2B newsletters that drive pipeline, build authority, and generate real revenue. - 115k+ subs in compliance - 7-figure ARR from email First 6 founders get theirs built free Reserve your slot here: https://www.spacebarstudios.co/inquire Running a business can feel like yo…
  continue reading
 
Running a business can feel like you're doing it all alone—but you don’t have to. Scalepath connects you with a private network of over 2,000 experienced operators, and CEO Rand Larsen will personally intro you to 3 like-minded business owners in your area. It’s part mastermind, part growth engine, part therapy. Book your free intro call at https:/…
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Running a business can feel like you're doing it all alone—but you don’t have to. Scalepath connects you with a private network of over 2,000 experienced operators, and CEO Rand Larsen will personally intro you to 3 like-minded business owners in your area. It’s part mastermind, part growth engine, part therapy. 👉 Book your free intro call at https…
  continue reading
 
Running a business can feel like you're doing it all alone—but you don’t have to. Scalepath connects you with a private network of over 2,000 experienced operators, and CEO Rand Larsen will personally intro you to 3 like-minded business owners in your area. It’s part mastermind, part growth engine, part therapy. 👉 Book your free intro call at https…
  continue reading
 
Scalepath connects you with a trusted network of over 2,000 business owners across the U.S. and Europe. Book a free call with CEO Rand Larsen, and he’ll personally introduce you to up to 3 vetted business owners in your region. Because in business, the right relationships change everything. Schedule your free intro call now: https://www.joinscalepa…
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Scalepath has a network of over 2,000 business owners across the U.S. and Europe. Book a call with the CEO Rand Larsen, he will introduce you to up to 3 business owners in your area. Relationships run the world, don’t forget that. Sign up for a free call here: https://www.joinscalepath.com/ Spacebar Studios is offering your company a free 90-day gr…
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Spacebar Studios is offering your company a free 90-day growth roadmap - Sign up for a free call here: https://www.spacebarstudios.co/ Scalepath has a network of over 2,000 business owners across the U.S. and Europe. Book a call with the CEO Rand Larsen, he will introduce you to up to 3 business owners in your area. Relationships run the world, don…
  continue reading
 
Spacebar Studios is offering your company a free 90-day growth roadmap - Sign up for a free call here: https://www.spacebarstudios.co/ Scalepath has a network of over 2,000 business owners across the U.S. and Europe. Book a call with the CEO Rand Larsen, he will introduce you to up to 3 business owners in your area. Relationships run the world, don…
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Sponsored by Spacebar Studios (https://www.spacebarstudios.co/) – your outsourced growth engine for B2B brands Peer Groups by ScalePath (https://www.joinscalepath.com/) – expert-led community for HoldCo builders Guest: Alex from RollUp Europe: https://rollupeurope.beehiiv.com/ Join us for a deep dive into one of the most fascinating stories in Brit…
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Dev Shah is the founder of Pocket Fund, a HoldCo that has acquired 7 businesses. At just 23, Dev has built a growing portfolio of newsletters, SaaS products, and mobile apps without raising a dime of outside capital. One of his first acquisitions, Sourcely.ai, made 37.5x MOIC. Thank you to our sponsors: Scalepath: https://www.joinscalepath.com/ Spa…
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