HoldCo Builders

PrivatEquityGuy

The HoldCo Builders Podcast with PrivatEquityGuy is a place where you can find meaningful conversations about holding companies, entrepreneurship, small businesses, investing, and more.Be sure to follow the podcast, so you never miss an episode!

  1. Buying 500+ Businesses and Turning $100k Into $10B - Fernando De Leon of Leon Capital Group

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    Buying 500+ Businesses and Turning $100k Into $10B - Fernando De Leon of Leon Capital Group

    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, healthcare, and technology. Capitalpad lets accredited investors co-invest deal by deal in curated, cash-flowing SMB acquisitions led by searchers and independent sponsors. Get a full deal room—financials, tax returns, sponsor profiles, and value-creation plans—then invest from $25k. These are long-term, illiquid investments and involve risk. Apply at: https://capitalpad.com/ Want brokers, operators, and investors to think of you first? That’s why I partner with Spacebar Studios—they build and scale B2B newsletters. They’ll set up your newsletter, send your first few editions, and prove the channel works—no fees, zero risk. They’re offering three HoldCo Builders listeners a free two-week trial. Go to: https://www.spacebarstudios.co/inquire You’ll learn: 00:00 - Intro & Leon Capital Group overview 02:26 - Border-childhood & immigrant mindset 05:24 - Turning labor into equity at 14 07:21 - Harvard takeaways & Goldman “pipes of money” 12:37 - Four questions to decode deal headlines 13:17 - Move to Dallas (2003) & flood-map/option flip 14:41 - Sponsor: CapitalPad 16:00 - 2008 crisis: speed over perfection; spouse’s push 17:21 - Going all-in 200×; distressed loans & 24-condo flip 18:04 - Broker flywheel & long-term loyalty 20:32 - Sponsor: Spacebar Studios 21:42 - PropCo/OpCo playbook → to 265 dental clinics 25:02 - Build it in-house: Patient Capital financing 25:51 - Cut out middlemen: insurance brokerage 26:41 - Crexi origin story: data, auctions, listings 28:38 - Wrap-up & next-episode teaser Support our Sponsors: CapitalPad: https://capitalpad.com/ SpaceBar Studios: https://www.spacebarstudios.co/inquire Subscribe on Spotify: https://open.spotify.com/show/6lr5bE3SNZF2uEE7Nb0DHh?si=cP_nAarhRmep1lvnR6uk5g Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/holdco-builders/id1695713724 Follow PrivatEquityGuy/Mikk Markus on Twitter: ⁠⁠https://x.com/PrivatEquityGuy This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions.

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  2. How I Bought 20+ Small Farms and Built a $350M HoldCo in My 30s | Jack McCarthy Interview

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    How I Bought 20+ Small Farms and Built a $350M HoldCo in My 30s | Jack McCarthy Interview

    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’re a searcher or operator and want real stories + actionable playbooks from the trenches, check the Scalepath newsletter and peer groups: https://scalepath.beehiiv.com/ Jack McCarthy, co-founder & CEO of Goldleaf Farming, shares how he’s building one of the largest specialty-crop platforms in the U.S. We cover why almonds & pistachios, raising $250M+, buying 20+ farms, and scaling to ~12,000 acres. Jack explains valuing farms by cash flow (not price per acre), managing water/climate risk, navigating commodity cycles, aligning with long-term LPs, and keeping leverage low. Timestamps: 00:00:00 Intro 00:00:28 What Goldleaf is building 00:01:26 Jack’s background & meeting co-founder Brandon 00:04:06 Wednesdays at the almond mill; lean-startup exploration 00:05:01 Partnership: Scalepath 00:06:26 Pivot from agtech to owning farms; meeting Brandon; first investors 00:09:48 Buying the first farm (Fall 2017) 00:10:35 Lessons from the first acquisition 00:14:10 Why almonds & pistachios 00:15:51 How they value farms (cash-flow/DCF mindset) 00:17:13 Partnership: Spacebar Studios 00:18:10 Capital raising phases (friends & family → family offices) 00:19:15 Alignment with LPs; team equity & structure 00:23:09 Diversified LP base (sub-$1M checks) 00:25:47 Capital structure: lower debt, higher equity 00:28:01 Biggest risks: water & growing conditions 00:29:09 Selectivity: ~1,400 farms reviewed; 27 bought 00:30:12 Early mistakes; refocusing on water/quality 00:32:02 Jack’s advice: constant improvement; long slog; do it 00:34:12 Personal Q: family (4 kids) 00:34:35 Culture & benefits: family-first values 00:36:57 Best investment advice & favorite book (East of Eden) ---------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/6lr5bE3SNZF2uEE7Nb0DHh?si=cP_nAarhRmep1lvnR6uk5g Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/holdco-builders/id1695713724 Follow Mikk/PrivatEquityGuy on Twitter: ⁠⁠https://x.com/PrivatEquityGuy This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions.

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  3. This Is the Best $1M EBITDA Business (A Lesson From Talking to 2,000 Business Owners)

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    This Is the Best $1M EBITDA Business (A Lesson From Talking to 2,000 Business Owners)

    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 real stories + actionable playbooks from the trenches, check the Scalepath newsletter and peer groups: https://www.joinscalepath.com/ Timestamps: 00:00:00 - Intro & guest: Rand Larson 00:01:43 - What ScalePath is (structure & purpose) 00:02:29 - “How I make money” 00:03:11 - HVAC acquisition near-bankruptcy story 00:05:07 - Genesis of peer groups (therapy → community) 00:06:43 - Ad break: Scalepath newsletter (sponsor) 00:07:49 - What makes a great event (small, similar, 3-hour format) 00:08:37 - Why local organizing is rare (and hard) 00:09:59 - Early peer groups = therapy; today = ROI focus 00:12:56 - 16 events in ~35 days 00:15:01 - Why paid improves attendance (Vistage/YPO comparison) 00:16:02 - Niche-based groups: B2B, pro services, local services 00:17:17 - Online vs. in-person 00:19:20 - Ideal setup: industry peers + local group 00:19:35 - Pricing models & member feedback 00:20:07 - Price point & ROI framing 00:22:32 - The van: $42k “vanlife” for meetups 00:23:10 - First trips & momentum 00:24:59 - Why the van is standout B2B marketing 00:25:59 - Newsletter stories: behind the scenes 00:27:47 - Why sell a commercial cleaning business 00:29:25 - Talking to $30–50M operators; misery check 00:30:38 - Community value for acquisition decisions 00:31:28 - Niche example: boat upholstery repair 00:32:59 - Hiring lesson: inexperienced vs. experienced owners 00:35:08 - Common theme: undercapitalization 00:35:33 - “Take every dollar the bank offers” (asset deal context) 00:38:29 - ~10% therapy; SBA-debt stress early on 00:40:16 - “Real work starts after close” 00:40:29 - Join a peer group before the fire (vs. during) 00:41:10 - Why experienced owners value peer groups ---------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/6lr5bE3SNZF2uEE7Nb0DHh?si=cP_nAarhRmep1lvnR6uk5g Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/holdco-builders/id1695713724 Follow Mikk/PrivatEquityGuy on Twitter: ⁠⁠https://x.com/PrivatEquityGuy This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions.

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  4. We closed 7 deals in 14 months (first $140m and a portfolio of 13 companies)

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    We closed 7 deals in 14 months (first $140m and a portfolio of 13 companies)

    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 launched for free. Reserve your slot here: https://www.spacebarstudios.co/inquire 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://www.joinscalepath.com/ Today’s guests are Lizzie Ryan and Darrel Connell, Managing Partners at IMBIBA, one of the UK’s leading specialist investors in leisure, education, and health. We cover IMBIBA’s operator-heavy model, why they back four-walls brands with proven unit economics, and how they sourced, structured, and exited deals through the toughest market in a decade. We dig into Fund I’s brutal raise, doing 7 deals in 14 months during COVID, building resilience in portfolio construction (childcare, wellness, and real estate-backed concepts), and the mechanics of operational gearing and like-for-like performance that drive exit timing. They share hard-won lessons on off-market origination (1,000+ outreaches → 600 meetings → 3–4 investments), upgrading teams post-investment, the “professional MD” hire, picking sites, saying no to bad leases, and aligning founder incentives with liquidity—without losing momentum. Timestamps: 00:00:00 Intro 00:00:07 Who are IMBIBA’s managing partners? 00:02:36 IMBIBA origin story & “two lives” of the firm 00:03:46 Fund I thesis: proven unit economics, operator help, rollout 00:04:22 Sponsor break - Scalepath 00:05:22 Building an operator-heavy PE team 00:06:11 Fundraising war stories (2018): the brutal last £10m 00:09:13 Post-raise: first 18–24 months 00:09:52 COVID hits: portfolio shut, scenario planning, survival 00:10:22 Doing 7 deals in 14 months: why founders chose them 00:11:35 What great PE–founder support looked like in crisis 00:14:19 Managing LP expectations during uncertainty 00:15:07 Rebuilding the portfolio: childcare, wellness, four-walls brands 00:16:14 Sponsor break - Spacebar Studios 00:17:35 Designing for resilience: margins, labor mix, exits 00:18:16 Portfolio & exits: NQ64, Little Houses Group 00:20:05 Who buys these assets now? (trade, PE, US interest) 00:21:49 When to sell vs. hold: operational gearing & like-for-like trends 00:25:18 Typical deal structure: significant minority, founder-led 00:26:14 Sourcing: mapping subsectors, off-market outreach 00:27:20 Upgrading teams post-investment; the “professional MD” hire 00:30:09 Funnel math: 1,000+ outreaches → 600 meetings → 3–4 deals 00:30:41 Red flags & when to walk at the 11th hour 00:31:43 Spotting real operators (site visits, staff, standards) 00:33:07 How their team works: operating partners on boards 00:34:57 Personal strengths & weaknesses (deal smell, negotiation) 00:37:23 Where founders need the most help: people & property 00:39:13 Coaching without micromanaging; the chair that moves the needle 00:41:28 Incentives & aligning around liquidity events 00:42:38 Navigating misalignment on timing and partial liquidity 00:45:06 Where they’ll invest next; where they won’t (exitability lens) 00:47:57 Supply of opportunities vs. capital in today’s UK market 00:48:44 Advice for emerging managers: resilience & learning from failure 00:50:01 What’s next

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  5. Larry Gagosian Makes $1B+ a Year Brokering Off-Market Art (While Still Owning 100% Of The Business)

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    Larry Gagosian Makes $1B+ a Year Brokering Off-Market Art (While Still Owning 100% Of The Business)

    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 didn’t wait alone; he built rooms full of people who moved. ScalePath surrounds you with like-minded operators so momentum compounds. Get 3 vetted intros for free. Book a call: https://www.joinscalepath.com/ A concise, hard-nosed breakdown of Larry Gagosian’s operator toolkit—how a relentless deal engine, secondary-market focus, and absolute control compound into 18 galleries and $1B in annual revenue. We translate his moves into actionable tactics for investors, business buyers and holding company builders: - build proprietary deal flow, - price on information, - create markets, - and turn relationships into leverage. Timestamps: 00:00:00 - Why Larry Gagosian 00:02:46 - Section 1: Build a deal engine 00:03:47 - Tactic: 100 cold calls a day 00:04:49 - Show up uninvited (crashing rooms, creating access) 00:06:04 - Default aggressive beats perfect timing 00:07:04 - Sponsor: ScalePath (operator network) 00:08:16 - Implementation: build your pipeline & momentum (questions to ask owners) 00:10:44 - Section 2: Total control and owning 100% 00:13:45 - Non-obvious plays (private-jet terminal gallery) 00:16:55 - Sponsor: Spacebar Studios (get your B2B newsletter built for free) 00:18:39 - Section 3: Build a market around your edge (secondary markets) 00:19:04 - Building a secondary market 00:21:19 - Tactics: proven assets, create liquidity, exploit fragmentation, earned secrets 00:23:06 - Apply to SMBs: secondary markets & roll-ups, own the transaction 00:25:58 - Investor lessons: ignore status games, price on info, map your niche, be the connector 00:26:37 - Section 4: Build relationships, not deals 00:27:31 - The S.I. Newhouse cold call and a life-changing relationship 00:29:04 - “Heir maps,” future inventory & proprietary deal flow 00:30:08 - Co-conspirators, not just clients (embedded trust) 00:31:03 - Operationalizing relationships (network, outreach muscle, non-transactional, real-world events) 00:33:44 - Think in decades (compounding relationships and capital) 00:35:24 - Synthesis: the Gagosian playbook (sell more, control, brand, secondary, outbound, relationships) 00:37:45 - Closing & CTA (share, subscribe, next episodes) ---------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/6lr5bE3SNZF2uEE7Nb0DHh?si=cP_nAarhRmep1lvnR6uk5g Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/holdco-builders/id1695713724 Follow Mikk/PrivatEquityGuy on Twitter: ⁠⁠https://x.com/PrivatEquityGuy This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions.

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  6. The Next Andrew Wilkinson? Building a 6-Company HoldCo (Bootstrapped with a 7-Figure Exit)

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    The Next Andrew Wilkinson? Building a 6-Company HoldCo (Bootstrapped with a 7-Figure Exit)

    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. Reserve your slot here: https://www.spacebarstudios.co/inquire Brandon Pindulic sold his first company for 7 figures, then built Space Bar Ventures — a bootstrapped holding company with 6 cash-flowing digital businesses and zero outside capital. We break down how he starts, buys, and scales companies, the $10K bet that launched his most successful venture, and the traps that kill most HoldCos. Timestamps: 00:00:00 - Intro 00:00:44 - Starting the first agency while working at a SaaS company 00:04:39 - Transition from side business to full-time entrepreneur 00:08:35 - Negotiation lessons and structuring the earnout deal 00:12:28 - Landing Oracle as first major client 00:14:06 - Post-sale period and consulting work 00:19:30 - Acquiring Planet Compliance - turnaround story 00:22:05 - Starting Spacebar Visuals with $10k and co-founder search 00:25:49 - Why the operator recruitment method works 00:28:54 - Refining Space Bar Ventures' vision – incubations vs acquisitions 00:32:36 - Sponsor: Spacebar Studios 00:36:15 - Advice for growing HoldCo Builders & Private Equity Guy 00:38:50 - Delegation lessons and becoming a better operator 00:42:42 - Spotting talent early - why Ryan was the right co-founder 00:44:32 - Current focus - growth over acquisitions 00:47:34 - Raising capital vs staying bootstrapped 00:50:02 - Cost-cutting and 'Vendor Day' – saving $100k/year 00:53:58 - Strengths, weaknesses, and growth strategy 00:57:35 - Why the $1M after-tax cash flow goal 01:01:24 - Quickfire: best investment advice & favorite books ---------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/6lr5bE3SNZF2uEE7Nb0DHh?si=cP_nAarhRmep1lvnR6uk5g Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/holdco-builders/id1695713724 Follow Mikk/PrivatEquityGuy on Twitter: ⁠⁠https://x.com/PrivatEquityGuy This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions.

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  7. How Michael Ovitz and Steve Schwarzman From BlackStone Find 10s

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    How Michael Ovitz and Steve Schwarzman From BlackStone Find 10s

    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 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://www.joinscalepath.com/ What if your next CEO hire could 10x—or destroy—your portfolio company? Michael Ovitz, legendary founder of CAA, built a $100M+ firm by spotting raw, misfit talent and turning it into power. In this solo episode, we break down the exact frameworks Ovitz used—and how HoldCo builders and investors can apply them to identify elite operators, structure trust systems, and build institutions that last. If you're hiring leaders, backing talent, or scaling a portfolio of companies—this is a playbook you can't afford to skip. Timestamps: 00:00:00 - Why Michael Ovitz Matters 00:05:07 - Big lessons when hiring a CEO for your portfolio company 00:05:25 - Sponsor: Scalepath 00:06:40 - Don’t overindex presentation and don’t judge by how equipped someone looks today 00:07:59 - Meet hundreds and thousands to train your eye 00:10:36 - Institutional momentum is more important than individual brilliance 00:16:32 - Sponsor: Spacebar Studios 00:17:59 - The top 0.01% of people I back just never stop 00:20:11 - Reward those who create a movement 00:22:28 - Decentralized decision-making 00:27:12 - Ego is the enemy of multiples 00:29:28 - Be brutally honest but relationship-driven 00:33:07 - Time is the ultimate enemy 00:36:14 - How to build time discipline in your investment firm or HoldCo 00:40:44 - Add these three questions to your DD 00:41:22 - How to win when you play the long game with people ---------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/6lr5bE3SNZF2uEE7Nb0DHh?si=cP_nAarhRmep1lvnR6uk5g Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/holdco-builders/id1695713724 Follow Mikk/PrivatEquityGuy on Twitter: ⁠⁠https://x.com/PrivatEquityGuy This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions.

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  8. How I Bought 4 Companies After Raising Millions from 35 Investors | Danny Vivier Interview

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    How I Bought 4 Companies After Raising Millions from 35 Investors | Danny Vivier Interview

    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 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://www.joinscalepath.com/ Danny Vivier is quietly building one of the most thoughtful vertical SaaS portfolios in the game. Buying founder-led software companies and grow them forever. Danny shares the real playbook behind Evermore's rise—raising from 35 investors, managing post-acquisition chaos, and why he's doubling down on boring businesses with big moats. Timestamps: 00:00:00 - Intro – Who is Danny Vivier? 00:01:07 - Starting First Landings (E-commerce) 00:02:10 - Product Sourcing and Early Days 00:03:09 - Getting Offer from Aggregator 00:04:56 - Sponsor: Scalepath 00:06:59 - Amazon Delisting Story 00:07:59 - Exit Process & Post-Sale Transition 00:08:42 - Why Danny Moved Into Software 00:09:30 - Managing Risk While Employed 00:11:22 - First Acquisition 00:14:34 - Sponsor – Spacebar Studios 00:16:06 - Partner Dynamics with Scott 00:18:04 - First Acquisition Size & Deal Terms 00:18:58 - Second Acquisition – Sign Company 00:20:03 - Launching the Evermore Strategy 00:21:08 - Lessons from Offline vs SaaS Businesses 00:22:05 - Post-Acquisition Leadership Hiring 00:24:14 - Offline Business Operations Today 00:25:13 - Going All-In on Vertical SaaS 00:26:36 - Acquisition Structures and Transitions 00:27:55 - Evermore vs VC, PE, and Search Funds 00:30:50 - Raising from 35 Individual Investors 00:33:00 - Convincing Investors with the Vision 00:34:50 - Investor Communication Systems 00:36:28 - Deal Sourcing Strategy 00:38:36 - Competition in Acquisitions 00:42:32 - Refining Acquisition Criteria 00:45:58 - Debt Strategy and Deal Structures 00:46:30 - Portfolio Size Today 00:47:03 - Doubling Down on One Platform 00:50:33 - Vertical SaaS Opportunity Ahead 00:51:04 - Current Portfolio Struggles 00:52:28 - Leaving Social Media 00:54:08 - Final Thoughts and Wrap-Up ---------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/6lr5bE3SNZF2uEE7Nb0DHh?si=cP_nAarhRmep1lvnR6uk5g Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/holdco-builders/id1695713724 Follow Mikk/PrivatEquityGuy on Twitter: ⁠⁠https://x.com/PrivatEquityGuy This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions.

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The HoldCo Builders Podcast with PrivatEquityGuy is a place where you can find meaningful conversations about holding companies, entrepreneurship, small businesses, investing, and more.Be sure to follow the podcast, so you never miss an episode!

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