Buyers and Builders

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 & discovering value investing
4:40 From NYU to Wall Street & joining a family office
7:58 Learning to analyze businesses & six key questions
10:33 Carvana deep dive: customer experience, lending & unit economics
17:03 Filtering noise, short reports & thinking in 10-year terms
22:21 Studying great long-term hedge funds & idea sourcing via 13F filings
25:17 Sponsor: Capitalpad - a marketplace for small business deals
26:19 What really matters: returns, time horizon & simple return math
36:16 When to sell: being wrong, better opportunities & thesis playing out
43:21 Leaving Wall Street for Buddhism & moving back to India
48:41 Enlightenment, meditation & inner transformation
55:21 Blending investing with spirituality, Substack & what’s next

Sponsored by CapitalPad:
https://capitalpad.com/ - A deal-by-deal private equity investing platform

Discuss investment ideas with Akshay: https://substack.com/@realreturns

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.

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 serial acquirers. After two decades mastering the art of permanent capital, Karlsson left to build his own vehicle. Six years later, RÖKO is worth billions.

TIMESTAMPS:
0:00 The hidden $2B holding company with 29 businesses
0:34 Who is Fredrik Karlsson? (Ex-Lifco CEO turned founder)
1:40 Röko’s launch: $20-25M founder capital + $200M raised
2:15 Portfolio breakdown: 29 companies across B2B and B2C
3:00 Q3 2025 results: 21% margins, 14.5% ROCE
4:46 How Röko scaled faster than any European serial acquirer
5:41 Why Röko only buys high-margin (15%+) asset-light companies
6:22 Sector-agnostic strategy and disciplined capital allocation
7:07 Risks Karlsson fears most: recession and bad managers
8:29 Röko HQ model: one Excel sheet, zero micromanagement

Sponsored by CapitalPad:
https://capitalpad.com/ - A deal-by-deal private equity investing platform

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.

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/ - A deal-by-deal private equity investing platform

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.

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
8:04 Shopify lesson: empathy that wins founders
11:54 David Cote at Honeywell: listening as diagnostic precision
15:47 How to practice it: questions, plant walks, and strategic silence

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/ - A deal-by-deal private equity investing platform

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.

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/ - A deal-by-deal private equity investing platform

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.

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/ - A deal-by-deal private equity investing platform

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.

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/ - A deal-by-deal private equity investing platform

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.

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/ - A deal-by-deal private equity investing platform

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.

Value-driven investor and turnaround specialist Reggie Pryor Jr. (Founder, Pryor 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/ - A deal-by-deal private equity investing platform

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 Pryor 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 Pryor 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 bas