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. Ian Rickwood on AI, Private Equity, Car Wash & Real Estate Investing | Henley Group

    1 G FA

    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 scale of Henley today: capital, sectors, and strategy 3:02 Early career: Procter & Gamble and Pepsi 5:02 Discovering Subway & winning the master franchise 7:04 “More margin in the lease than in the sandwich” real estate awakening 11:01 From 17 Subways to buying Benjys 13:03 Scaling Benjys to 90 stores + ~200 ‘vanchises’… then getting crushed 15:05 A tough exit and what it taught Ian 17:04 Starting Henley from lifestyle dev to serious platform 19:03 Surviving the GFC and pivoting the model 21:03 A 12-year run and Henley’s track record 22:07 Building a firm with your spouse “colors and numbers” 25:08 Bringing the kids into the business (without ruining them) 29:04 Dealing with bad deals and problem assets 31:02 Geographic expansion Holland, Germany, Poland, Ireland 33:06 Entering the US and timing the exit 33:56 From deal-by-deal to first fund 37:03 “It’s all about the deal” capital vs conviction 40:13 Sponsor: Capitalpad marketplace for acquisition deals 41:20 What a perfect operator/entrepreneur partner looks like 43:03 Reading people in a 60-minute meeting 45:02 Why car washes? Entering a ‘boring’ but beautiful business 47:03 The failed first platform: overpaying, over-spending, bad sites 48:00 Rebuilding from scratch: launching Aquasonic the right way 49:02 Data, AI and picking car wash sites 52:05 The most expensive beliefs Ian has changed 55:11 Big-picture lessons keep learning, don’t give up, pivot fast 57:17 Favorite books and how Ian unwinds 57:47 Closing thoughts and wrap-up  Sponsored by CapitalPad: https://capitalpad.com/ Follow Mikk/PrivateEquityGuy 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.

    58 min
  2. The Private Equity Bubble? | Inside a Private Equity Firm Built for What Comes Next

    6 GG FA

    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 middle market. 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, or you want to back great operators, visit https://capitalpad.com/ Our sponsor Spacebar Studios builds and runs your newsletter end to end, so you stay top of mind with founders, brokers, LPs, talent and your customers without adding to your workload. Strategy, writing, design, sending, and list growth are handled. HoldCo Builders listeners also get a two-week free trial. Start with a free intro call at https://www.spacebarstudios.co/inquire TIMESTAMPS 0:00 Intro 5:03 Focus: diversified industrials & business services 6:27 Hold period philosophy 7:07 Target size & screens 8:04 Why pursue larger deals 9:41 Value creation beyond capital; control investing 11:08 Hands-on operations (presence on the floor) 12:53 Sponsor: CapitalPad 14:16 Stewardship playbook: cost discipline, systems, people 15:24 Beyond the P&L: culture & morale 16:18 Weighing purpose vs. numbers 21:42 Factory-floor insights you won’t see in a data room 25:48 Why deal flow is “easy” (but a lot of work) 28:16 Sponsor: Spacebar Studios 29:48 Bigger vs. smaller deals 31:44 Seller types: family, PE, and carve-outs 33:50 Winning trust with founders not yet selling 38:02 Where the best off-market deals originate 39:10 Time allocation & focus blocks 41:05 Best ROI: banker processes vs. proprietary 43:40 Deals that die… and come back 44:51 What’s exciting now: volatility & tariffs 47:12 Patterns of elite operators 49:24 Staying sharp & never settling 53:16 War stories from the trenches 55:15 What’s next for Woodson (2-3 years) 57:08 “No bad deals, only bad prices” 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.

    1 h
  3. The One System That Scaled from $3.5M to a 15-Company Portfolio (Sid Jashnani)

    4 NOV

    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, or you want to back great operators, visit https://capitalpad.com/ Our sponsor Spacebar Studios builds and runs your newsletter end to end, so you stay top of mind with founders, brokers, LPs, talent and your customers without adding to your workload. Strategy, writing, design, sending, and list growth are handled. HoldCo Builders listeners also get a two-week free trial. Start with a free intro call at https://www.spacebarstudios.co/inquire We discuss: 0:00 Intro: from systems integrator to 15-company HoldCo 0:34 Plateau at $4M: what wasn’t working 3:22 Discovering EOS: why it clicked and how to start 7:46 Sponsor CapitalPad: accredited investors invest in acquisition entrepreneurs 10:26 Owning product lines: vertical integration and moat 16:59 Rolling EOS across companies: the non-negotiable cadence 18:05 Before vs after EOS: escaping firefighting and gaining control 19:19 Sponsor Spacebar Studios: done-for-you newsletters for deal flow and trust 24:02 Accountability Chart: firing yourself from Ops the right way 29:05 Hiring via scorecard: finding the operator who can deliver 37:20 Eight Cash Drivers: terms, inventory discipline, margin expansion 49:02 Portfolio snapshot: 15 companies and current metrics 52:44 Build vs buy: when to create your own product 1:03:00 Raising a fund: de-risking and scaling the platform 1:06:54 Partnering with PE: timing, structures, and trade-offs 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 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.

    1 h 11 min
  4. 7 Acquisitions Done — Buying Businesses on “Easy Mode” in 2025 (here’s why)

    31 OTT

    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 cover: 00:00 Intro — making buying businesses & raising capital easier 00:27 Danza’s path: IB/PE → Clear Peak → the CapitalPad problem 02:01 Travis’s path: founder → exits → discovering SMB deals 03:35 Why SMB acquisitions: return studies & the access gap 05:11 The marketplace solution: deal flow + right-sized checks 06:45 Build & launch timeline; choosing curation over “open” 07:46 Fees & alignment: investors pay (20% carry + 1.5% close), sponsors free 10:36 Curation filters: leverage, concentration, valuation, tough industries 15:13 Do good deals fund? Understanding complexity & platform growth 16:51 Searcher flow: teaser, VDR, interview, listing, go-live 18:02 Investor experience: NDAs, Q&A, allocations, SPV mechanics 19:54 Post-close: reporting discipline & early outcomes 21:42 Portfolio design: illiquidity + diversify (expect some failures) 22:45 Market temperature: pricing sanity, avoiding froth 23:55 Common searcher mistakes; why post-LOI matters 27:33 Beyond capital: better governance 31:01 No pay-for-priority access; keeping incentives aligned 32:14 Roadmap: expert LP involvement & operator support 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.

    33 min
  5. How to Build a 7-Figure Company from Scratch (with Mac Lackey)

    27 OTT

    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: 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, or you want to back great operators, visit https://capitalpad.com/ Our sponsor Spacebar Studios builds and runs your newsletter end to end, so you stay top of mind with founders, brokers, LPs, talent and your customers without adding to your workload. Strategy, writing, design, sending, and list growth are handled. HoldCo Builders listeners also get a two-week free trial. Start with a free intro call at https://www.spacebarstudios.co/inquire We discussed: 0:00 Who is Mac Lackey + Spanish football club owner 0:34 Early life: football-first, scholarship, brief pro career 1:28 First company 3:06 Early internet wave (1998 eight-figure exit in mid-20s) 5:24 Post-exit: acquirer IPOs (’99); starts a football media company 9:08 Building the largest non-televised football content shop:14-month sale (2000) during dot-com crash 12:20 The “strategic value vs financials” lesson and buyer’s lens 14:50 Sponsor: CapitalPad 20:14 Engineering a bidding war in London; fast LOI from competitors 27:53 Sponsor: Spacebar Studios 29:02 Third company: interim CEO, roll-ups, misaligned risk appetites and sells stake (which later becomes a nine-figure outcome) 33:23 Life design shift: optimizing for freedom of time after first child 48:08 Exit DNA: optionality, 10–100x ROI examples; common fixes (founder dependency, buyer math, estate/tax prep “two years + 1 day”) 1:02:52 Bet on people Support our Sponsors: CapitalPad: https://capitalpad.com/ SpaceBar Studios: https://www.spacebarstudios.co/inquire Reach out to Mac: https://maclackey.com/mikk/ 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.

    1 h 5 min
  6. How Builders Build Wealth That Lasts (and Mistakes to Avoid)

    25 OTT

    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 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, or you want to back great operators, visit https://capitalpad.com/ We break down the three pillars of lasting wealth: 0:00 The hidden question after success: what do you do with the money? 1:30 Builders vs. stewards: different skill sets, same discipline 2:00 How legacy families preserve wealth for generations 2:30 "From rice field to rice field" 4:00 The simple fundamentals wealthy families follow 4:20 Why complexity sells, but simplicity endures 5:45 The two-bucket philosophy: preservation and compounding 6:01 Pillar #1: Conservative fixed income (your stability base) 6:40 Story: The entrepreneur who lost half his fortune chasing returns 7:22 Sponsor: CapitalBad - the marketplace for long-term investors 8:16 Pillar #2: High income strategy (living off cash flow) 9:12 Example: The Midwestern family that compounds quietly 9:15 Pillar #3: Long-term growth (own great companies for decades) 10:05 Compounding only works if you let it 10:59 Consumption vs. compounding: every generation’s choice 11:45 Structure, simplicity, and temperament in wealth management 12:00 Can you manage yourself as well as you managed your company? Support our Sponsor: CapitalPad: https://capitalpad.com/ 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.

    13 min
  7. 4 Portfolio Companies and The Gritty Playbook of Value Investing | Reggie Pryor Jr.

    21 OTT

    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 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, or you want to back great operators, visit https://capitalpad.com/ Our sponsor Spacebar Studios builds and runs your newsletter end to end, so you stay top of mind with founders, brokers, LPs, talent and your customers without adding to your workload. Strategy, writing, design, sending, and list growth are handled. HoldCo Builders listeners also get a two-week free trial. Start with a free intro call at https://www.spacebarstudios.co/inquire Timestamps 0:00 Reggie Prior Jr. and his “buy overlooked, rebuild cash flow” playbook 0:50 Wofford College and mentor Jimmy Gibbs 3:57 The lesson: just ask (how Reggie earned the mentorship) 5:16 Running his father’s company; learning by doing 9:43 Sponsor: CapitalPad (operator-investor marketplace) 11:05 Reframing the strategy: rebuild rather than break apart 12:42 Prior LLC’s four pillars (Diversified, Global, CRE, Capital) 13:30 Why he rarely sells 15:02 Portfolio overview; value lens across categories 16:48 Case study: Highway 9 real-estate deal 19:59 Adding 265k of value by acquiring a state-owned strip for $12,000 22:41 Sponsor: Spacebar Studios 27:05 Where private deal flow comes from 27:57 Moretex origins (founded 1908) and how he stumbled onto the opportunity 31:10 Hidden kicker: next door 70 million dollar stadium 32:12 Taking over Moretex 33:50 Lessons from doing the deal and showing up personally 34:13 First 90 days: key hires (maintenance, SOPs); no salesperson for 31 years 35:52 Vertical integration: buying the pulverizer supplier 38:00 Tariff tailwinds plus all USA inputs boost demand 38:21 Oldest chemical plant in the Southeast 41:37 Brand and formula value 42:56 Why no auction? Family context, timing, and trust 44:13 Mission: fix and own Moretex long term 45:44 Building a mentor bench: the names and why it matters 47:02 Three “secrets” 48:09 How networks actually compound (and how to start) 51:04 Reggie works seven days a week, 365 days a year 52:59 On happiness, overwhelm, and tradeoffs 55:49 Why saving American manufacturing is personal 58:33 How picky is he? On saying yes, triaging inbound, new bets 1:00:39 Why do the podcast? On signal, diligence, and reciprocity 1:02:08 Wrap up: key lessons and gratitude 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 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

    1 h 4 min

Descrizione

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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