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From VC to Main Street: How AI Is Rewiring Service Businesses
3 december 2025 · 52 min
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. Lees meer
Cyrus has lived every chapter of the operator-investor journey: aerospace engineering, Salesforce sales, venture capital, architecting AI rollups at OpenOcean, and now backing searchers at Shore Capital Partners.
We dive into how AI is transforming traditional service industries, where real opportunities (and risks) lie, how to evaluate founders, and why the best investing often happens in industries that don’t change.
TIMESTAMPS:
0:00 Cyrus’s operator & investor journey
2:02 Spotting the tech gap in the traditional economy
3:43 Data infrastructure, MySQL roots & AI rollups at OpenOcean
5:15 Bridging VC, AI and micro-cap PE
8:37 What AI-enabled services really are (with simple examples)
12:21 Inside OpenOcean’s AI-enabled services thesis & deal work
16:00 Joining Shore Capital & backing searchers and roll-ups
18:14 How Cyrus evaluates AI risk and upside in real deals
31:01 Moving from VC to ETA/PE and key mindset shifts
45:46 Investing in what doesn’t change, AI as a tailwind & favorite bookFollow 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.
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How to Find 10x MOIC, 30%+ IRR Deals (Step-by-Step)
28 november 2025 · 19 min
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. Lees meer
You’ll learn why your portfolio will never be “the index”, how a tiny % of deals drive almost all returns, and what elite investors do differently to consistently catch those outliers. If you’re a searcher, investor, fund, or holdco, this is the episode that will change how you think about ETA returns forever.
TIMESTAMPS
0:00 Access as the #1 driver of outperformance & episode roadmap
0:40 Dinner scene: Stanford-slide searcher vs seasoned LP reality
2:15 Power laws, Magnificent Seven & how a few winners drive all returns
3:40 Yale study: 1,192 investor observations vs the Stanford search fund myth
5:35 Segment 1: The Illusion of the Stanford Index & why no one matches it
7:45 Segment 2: The Batting Cage Problem & why access determines investor outcomes
9:26 Segment 3: The Two-Stage Bet, broken searches, missing winners & 10x outcomes
15:20 Elite ETA investor tier, access hierarchy & why “spray and pray” fails
17:51 Real odds for searchers, importance of elite access & final “respect the griffins” takeaway#ETA #SearchFunds #EntrepreneurshipThroughAcquisition #SelfFundedSearch #TraditionalSearch #SearchFundInvestor #SearchAcquisition #BusinessAcquisition
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.
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I Bought 20 Companies (Here's What I Learned) | Sequoya Borgman Interview
25 november 2025 · 1 uur 3 min
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. Lees meer
In this episode, we break down how he sources mostly off-market deals in second-tier cities, structures conservative, over-capitalized balance sheets, manages messy founder transitions, and keeps hundreds of retail LPs aligned while staying oversubscribed on almost every deal.
TIMESTAMPS
0:00 Biggest risk in PE founder transitions and bad leadership fit
0:44 Why the “retail private equity” model
4:37 Working with PE as a CPA and deciding to start Borgman Capital in 2017
6:10 How uncertainty really hits lower middle-market companies
8:04 Biggest early mistakes: Hiring the wrong leaders and underestimating founders
11:35 Responsibility to employees, banks and LPs
14:12 First acquisition story
16:24 Why Borgman chose hundreds of retail LPs instead of a fund
20:45 Oversubscribed deals, memos, webinars and passthehat.com
30:23 State of private equity today: Fewer deals closing, lower leverage and patient sellers
32:34 Why Borgman fishes in second-tier cities
36:17 Deal flow: 1,500 deals a year, 2-minute financial test and what they actually buy
40:49 Adding 500k-1M of extra equity to protect against surprises
54:44 Risks of raising from regular investors
58:59 When to sellFollow 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.
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How I Retired at 30 as a Family Office Investor (Here Are the Investments I've Made)
20 november 2025 · 1 uur 1 min
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. Lees meer
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
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 nextDiscuss 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.
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Buy 5 Companies as Fast as You Can (1-on-1 Advice From Fredrik Karlsson That Changed Everything)
17 november 2025 · 12 min
There’s a holding company that almost no one talks about, yet it might be one of the most efficient compounding engines. Lees meer
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 micromanagementFollow 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.
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Ian Rickwood on AI, Private Equity, Car Wash & Real Estate Investing | Henley Group
14 november 2025 · 58 min
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. Lees meer
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
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-upFollow Mikk/PrivateEquityGuy on Twitter: https://x…
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How to Win Deals Over Private Equity (Even if They Pay 10-20% More)
12 november 2025 · 24 min
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. Lees meer
#BusinessAcquisitions #DueDiligence #MergersAndAcquisitions #HoldCoBuilders
#ListeningSkills #DealMaking #EntrepreneurshipThroughAcquisition #PrivateEquity #BusinessBuying #SMBacquisitionTIMESTAMPS
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 -
The Private Equity Bubble? | Inside a Private Equity Firm Built for What Comes Next
9 november 2025 · 1 uur
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. Lees meer
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)
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)
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.
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The One System That Scaled from $3.5M to a 15-Company Portfolio (Sid Jashnani)
4 november 2025 · 1 uur 11 min
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. Lees meer
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
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
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-offsSubscribe on Spotify:
https://open.spotify.com/show/6lr5bE3SNZF2uEE7Nb0DHh?si=cP_nAarhRmep1lvnR6uk5gSubscribe on Apple Podcasts:
https://podcasts.apple.com/us/podcast/holdco-builders/id1695713724Follow 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 Acquisitions Done — Buying Businesses on “Easy Mode” in 2025 (here’s why)
31 oktober 2025 · 33 min
Buying a small business and raising the equity shouldn’t take a roadshow. Lees meer
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.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 supportSubscribe on Spotify:
https://open.spotify.com/show/6lr5bE3SNZF2uEE7Nb0DHh?si=cP_nAarhRmep1lvnR6uk5gSubscribe on Apple Podcasts:
https://podcasts.apple.com/us/podcast/holdco-builders/id1695713724Follow 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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How to Build a 7-Figure Company from Scratch (with Mac Lackey)
27 oktober 2025 · 1 uur 5 min
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. Lees meer
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.
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
20:14 Engineering a bidding war in London; fast LOI from competitors
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 peopleReach out to Mac: https://maclackey.com/mikk/
Subscribe on Spotify:
https://open.spotify.com/show/6lr5bE3SNZF2uEE7Nb0DHh?si=cP_nAarhRmep1lvnR6uk5gSubscribe on Apple Podcasts:
https://podcasts.apple.com/us/podcast/holdco-builders/id1695713724Follow 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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How Builders Build Wealth That Lasts (and Mistakes to Avoid)
25 oktober 2025 · 13 min
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? Lees meer
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.
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
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?Subscribe on Spotify:
https://open.spotify.com/show/6lr5bE3SNZF2uEE7Nb0DHh?si=cP_nAarhRmep1lvnR6uk5gSubscribe on Apple Podcasts:
https://podcasts.apple.com/us/podcast/holdco-builders/id1695713724Follow 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 Portfolio Companies and The Gritty Playbook of Value Investing | Reggie Pryor Jr.
21 oktober 2025 · 1 uur 4 min
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. Lees meer
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
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
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, diligen… -
How They Turned $8 Million into $450 Million (by Following THIS #1 SIMPLE Habit)
19 oktober 2025 · 13 min
The greatest builders in history share one habit that changed their fortunes. Lees meer
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.
Timestamps
0:00 Intro: The compounding power of reading0:49 Investor quotes on reading
2:04 A real competitive advantage
2:32 A 50-year habit and the $500M outcome
3:25 The Tenecco idea and the $8M to $80M jump
5:52 Jeff Bezos: One stat that launched Amazon
6:09 Morris Chang (TSMC): A textbook insight that rewired an industry
6:36 Elon Musk: no Mars plan
6:50 Dietrich Mateschitz
7:11 Bill Gates: The Altair 8800 moment
7:25 Phil Knight: Japanese trade finance to Nike’s supply chain
8:55 Naval Ravikant on lifelong reading
10:27 $8M to $80M to $500M
10:50 “5 to 10 great insights in a life”
11:40 The 29x BYD outcome
11:48 How reading trains intuition: “You can almost smell it”
12:22 The ultimate unfair advantage of reading
13:00 Final challenge: Are you reading like your life depends on it?
Subscribe on Spotify:
https://open.spotify.com/show/6lr5bE3SNZF2uEE7Nb0DHh?si=cP_nAarhRmep1lvnR6uk5gSubscribe on Apple Podcasts:
https://podcasts.apple.com/us/podcast/holdco-builders/id1695713724Follow 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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How to Build Proprietary Deal Flow? (15 Off-Market Acquisitions)
16 oktober 2025 · 29 min
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: Lees meer
- 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 owner about selling - someone in the room even booked a meeting before lunch.
Timestamps
00:00 One-day M&A Lab
01:41 The scary 3-5 year goal (Fund II at $50M, 5× MOIC ambition)
03:00 The math behind 5×: low entry multiples, modest growth, sane leverage
06:47 Scaling a bigger fund by doubling down on winners via add-ons
07:49 “Every business problem can be solved through M&A”
09:58 Most underrated outreach
11:12 The only goal of the first call
12:55 The 128-question pre-LOI audit
16:24 “Pre-diligence” naming hack to get real docs before LOI
18:54 Three-phase diligence
21:55 Winning competitive processes by showing deeper prep
22:30 How pre-LOI depth prevents post-LOI drama
23:32 Selling = buying in reverse
25:54 Huge ROI on practitioner-level M&A education
27:02 Why his big goal now feels closer
28:39 Why Grant’s clarity matters in dealsSubscribe on Spotify:
https://open.spotify.com/show/6lr5bE3SNZF2uEE7Nb0DHh?si=cP_nAarhRmep1lvnR6uk5gSubscribe on Apple Podcasts:
https://podcasts.apple.com/us/podcast/holdco-builders/id1695713724Follow 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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Lessons from 100+ Acquisitions You Can Implement TODAY | Joe Liemandt
12 oktober 2025 · 29 min
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. Lees meer
Timestamps
00:00 Intro: Who is Joe Liemandt & why this episode
01:16 The real job of a boss: raise the bar
03:25 Reality-distortion & Trilogy’s elite culture
06:44 Expect more than they expect of themselves
08:46 ESW Capital’s “insane” bet: buying legacy software
12:47 Pricing power: why most companies undercharge
14:33 Value-based pricing: the ESW playbook
16:15 Pricing moats
17:56 The real bottleneck: motivation vs information
19:48 Hiring for fire
21:27 Inner scorecard
23:12 Information is commodity; motivation is scarcity
24:45 Leaders as motivators
26:10 Systems that reward curiosity, not compliance
27:06 Closing framework: light the fire
27:55 “Customers have the answers” - sit with end usersSubscribe on Spotify:
https://open.spotify.com/show/6lr5bE3SNZF2uEE7Nb0DHh?si=cP_nAarhRmep1lvnR6uk5gSubscribe on Apple Podcasts:
https://podcasts.apple.com/us/podcast/holdco-builders/id1695713724Follow 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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How We Bought 27+ Businesses and Built a $1 Billion HoldCo at 39 | Steve Carroll Interview
7 oktober 2025 · 1 uur 11 min
Steve Carroll is the CEO & co-founder of Kelso Industries, a national MEP services platform uniting HVAC, mechanical, plumbing, and electrical companies. Lees meer
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 model, how they finance growth without overpaying, and the operating system (recruiting, cash, WIP discipline) that lets local brands scale without losing their soul.Timestamps
00:00 Intro
00:34 Steve’s background
01:56 Early thesis: from marketing & home services lead gen to HVAC focus
03:54 Bootstrapping experiments, agencies, pest control—what worked/what didn’t
04:58 Personal runway & the real cost of chasing deals while employed
06:00 Broken deals, travel, and swallowing $100k–$200k before first close
06:16 Meet the co-founder: lifelong friend Steve Nicholson; Kelso name origin
08:32 First near-deal dies; deciding to swing at the largest SBA-sized deal
10:26 Finding a commercial HVAC business in Arizona
18:23 Survival year: no new acquisitions, just fixing ops and cash
19:13 The unlock: partnering with an Idaho operator who stays on, not exits
20:21 Bringing in a PE partner (Peterson Partners): why working capital blew up the SBA plan
24:26 How the PE check actually changed things (and what it didn’t)
29:32 Scale after deal #2: ~$40–50M revenue; raising the bar to $30–40M targets
30:50 Handing Arizona to Poncho so Steve can live on planes finding partners
33:22 Hitting $10M EBITDA in 2 years and setting the $1B revenue goal
34:32 Reaching $1B TTM four years after launch
36:25 Structure: Kelso buys 100%, owners stay, roll equity, 3-year earnouts
37:48 Why this is a relationship business (and why replacing owners destroys value)
43:10 Liquidity: horizon to public markets or n… -
How I Completed 12+ Acquisitions and Still Built a New Roll-Up
4 oktober 2025 · 53 min
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: Lees meer
- to independent sponsorship,
- lessons from 12+ acquisitions,
- what makes a good business model,
- partnering with operators,
- and buying seller-dependent companies.We cover:
0:00 Nick Hatchka on 12+ acquisitions and a California generator platform
0:35 Background: MIT → McKinsey → 2 startups → Fortune 500 clean tech
1:54 Founding Cub (2016): SBA and personal capital for the first deal
2:49 Scaling: 12+ acquisitions across interior plants and landscaping, later divested
4:09 New platform thesis: generators in California and why the model is capital intensive
5:27 Investing focus: market and model selection over operator heroics
8:16 Capital discipline: self-funded pace vs raising outside capital
12:03 Generator business explained: sell, install, maintain, and test backup power (monthly, quarterly, annual PMs)
20:11 Partnering with Dylan Ferguson: 20-30 interviews and complementary skills
25:54 First acquisition Conti: sourced direct, LOI-to-close ~6 months, closed Jan 2024
28:16 Post-close playbook: replace owner-operator and rebuild systems for scale
33:39 Early lessons: grew fast to replace 4–5 seller hats and would build recruiting pipeline earlier
34:38 Results: revenue ~$3M → ~$6M and team 7 → ~14
42:13 Second acquisition PowerGen: 5–6 months later with larger C&I footprint in Bay Area and Sacramento
45:04 Capital and operating philosophy: seller note fixed ~8 years, target ≥3x DSCR, keep strong cash reserves and focus on service quality
51:32 Book and wrap: The Science of Success and expanding the circle of competenceSubscribe on Spotify:
https://open.spotify.com/show/6lr5bE3SNZF2uEE7Nb0DHh?si=cP_nAarhRmep1lvnR6uk5gSubscribe on Apple Podcasts:
https://podcasts.apple.com/us/po… -
How to Raise $450 Million at 31 with No Track Record (and Do 90+ Deals) | Urs Wietlisbach Research
30 september 2025 · 26 min
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.) Lees meer
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.
You'll learn:
00:00 Why this episode & who it’s for
00:36 From “stocks & bonds are boring” to real assets; early AUM context
01:25 Independence as the goal; raising $450M with no track record
02:20 Three complementary founders is better than one “perfect” entrepreneur
03:12 Leaving Goldman: the coffee invite, risk, and family pushback
04:35 “Fill your backpack”: learn aggressively, then have the courage to leave
05:43 The costly fundraising mistake: paying an upfront “rainmaker” (and why never again)
06:40 Why they IPO’d in 2006: talent, direct deals, and Asian credibility
10:05 Operating public, thinking private: ignore the ticker, focus long term
10:30 “We are responsible for dreams”: pensions as the true client
11:05 Proactive diligence: working 12–36 months before a sale is announced
12:05 Urs’s role today: fundraising, client relationships, and a 100+ person marketing team
12:45 The PE model now: ~53% equity / 47% debt; returns from business building
13:35 Edge vs. competitors: thematic sourcing and pre-work win auctions
14:40 Example: German deal log, 582 days of prep before the bank book
16:05 Returns stack vs. mega-peers; tailwinds, management being everything
17:13 Four thematic teams: Healthcare, IT, Goods/Products, Services
18:00 Healthcare thesis in action: U.S. physiotherapy roll-up playbook
19:10 From 100 to 600+ clinics; EBITDA from ~$38M to ~$110M in four years
19:56 Why PE has outperformed publics: information, incentives, not leverage
21:00 Compensation design: “eat what you kill” + shared carry across teams
21:50 Hiring from industry, not just finance; sweat equity for managers
22:40 Heav… -
9 Figure Exit How I Built and Sold to Private Equity (Alexis Sikorsky Interview)
27 september 2025 · 1 uur 19 min
My guest today is Alexis Sikorsky. An entrepreneur who bootstrapped, scaled, and ultimately sold a company in a 9-figure exit. Lees meer
We cover:
00:00 Intro
01:36 Who is Alexis Sikorsky
02:03 Early entrepreneurship
03:59 First ISP & internet café in West Africa
05:12 Conflict with government & partner’s death
07:05 Buys training company
07:43 1999–2000: founding the software dev firm
09:20 Buying assets of Logical Access
09:37 On failures & lessons (politics, client concentration)
12:35 “I can’t be employed” mindset / drive to continue
13:06 2008 peak: €11–12M revenue, €3M profit
14:31 “The grind” years: cuts, mortgages, survival
15:17 Private equity calls
16:35 The very optimistic 2-year plan
17:22 The deal: ~11x EBITDA, 85% cash now / 15% later
18:59 Final personal exit; later strategic sale (undisclosed 9 figures)
20:41 “If I had 2023 wisdom in 2003…”
21:22 How much runway to hold; agility for black swans
22:23 Fear, resilience, and hiring “good people” too late
24:59 Personality under stress; heart attack joke
28:07 Why post-PE period was the best
28:13 “Did you sell to the right people?”
28:29 Strengths & weaknesses
30:00 Life after exit
34:31 What retirement actually felt like
35:01 Happiness, safety, safari/diving; minimal “stuff”
39:52 Founders often don’t know their own company
40:52 Know your numbers monthly
43:28 “Fire yourself” from most tasks as CEO
44:51 “What’s your number?” conversation
45:37 Grow to sell vs. morphing into a bank
47:50 Growth vs. lifestyle businesses
50:16 Execute phase cadence
51:08 Best growth levers (context-dependent)
52:03 M&A focus for this audience
52:17 Why M&A is the fast/cheap shortcut
54:01 Leverage math in euros (LBO example)
56:08 PE myths
1:01:05 Negotiate your own contract & non-compete
1:01:23 Managing time during diligence
1:02:21 Readiness test: 1-week no-phone vacation
1:02:37 How to diligence PE (ask for 5, call the others)
1:06:59 What buyers saw that he didn’t
1:10:41 Why founders often under-sell
1:10:55 Nominal EBIT… -
He Bought 4 Small Businesses with ZERO Finance Experience (Nikolai Dimitrov Interview)
23 september 2025 · 41 min
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. Lees meer
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.
We'll cover:
00:00 Intro: Who is Nikolai Dimitrov & Unity Investment Partnership
00:26 From pro football to acquisitions: quitting and what came next
02:04 Why buying companies: passion, team skills from sport
06:22 First strategy: veterinary roll-up
10:36 12-18 months with no deal: iterate, don’t quit
11:50 First acquisition: 4× cash flow; 25% down, 75% seller-financed
13:35 Year 1 reality: building reporting from scratch in a mom-and-pop
14:53 “Terms over price”: negotiating when you’re the only buyer
17:34 Closing the first deal: proof the model works in CEE
18:34 Seller pipeline tailwind: retiring baby boomers in small business
21:35 Raising from LPs: doctors, lawyers, real estate pros
22:50 Second acquisition; time allocation across businesses
23:33 Third deal: dental clinic
25:15 Incentives and the shift from deal-making to asset management
26:58 What a “good deal” looks like; buying right at low multiples
32:31 Growing the portfolio: sector differences, ops cadence
33:59 Diversified vs focused holdco: trade-offs in reporting & speed
35:10 Holdco vs fund: why avoid a limited-life vehicle (for now)
37:55 Best advice: a few winners drive returns (Buffett lesson)Subscribe on Spotify:
https://open.spotify.com/show/6lr5bE3SNZF2uEE7Nb0DHh?si=cP_nAarhRmep1lvnR6uk5gSubscribe on Apple Podcasts:
https://podcasts.apple.com/us/podcast/holdco-builders/id1695713724Follow Mikk/PrivatEquityGuy on Twitter: https://x.com/PrivatEquityGuy
This podcast is for informational purposes only and should not be relied upon as a bas…
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I Raised $11.7M To Back 13 Self-Funded Searchers | Grant Hensel Interview
20 september 2025 · 51 min
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. Lees meer
If you’re buying or backing boring, profitable businesses, this is a playbook episode.
You'll learn:
00:00 Grant’s path: 10 starts, 2 exits, 1 scaled; now backing self-funded searchers
00:32 Grant’s background & living the “buy vs. build” debate
02:26 Buying a business for his wife to run (4 LOIs, funny diligence misses)
05:24 First 90 days: installing EOS, weekly scorecard, real traction
06:52 Portfolio before the fund (one built, one bought)
07:59 Holdco vs. minority investing; why operator quality dominates
09:32 Why self-funded search is a built-in grit test
10:14 From personal checks to raising a fund (organic evolution)
12:23 The four screens: low concentration, low capex, low cyclicality, history of profits
13:53 Cyclicality lesson: cheap isn’t worth macro sensitivity
15:52 Fund timeline: Oct ’24 idea → Feb ’25 start → Jul ’25 close
16:39 Fundraising tactics: “ask for advice,” webinars, soft-circle snowball
20:27 Looking at deals while raising; confidence once ~$5M soft-circled
21:16 How Grant picks winners: on-site diligence, non-spreadsheet reality
22:51 Sourcing searchers: Searcher.com, webinars, “This Week in ETA” newsletter
26:15 Day-to-day now: LOI diligence, marketing, advisor feedback (pre-first deal)
27:17 Deployment pace: 13–18 deals over 2–3 years (~1 every other month)
27:38 Deal flow volume: ~1 LOI/day; be ultra-selective
28:03 The five pre-LOI seller questions (and why they matter)
32:26 What to buy (and avoid): home/B2B services, light mfg (with chops); no e-comm/retail/restaurants
33:58 The real investor value-add: resilience through the ugly middle
35:18 Roll-up skepticism; single-asset cash flow is better than multiple-expansion bets
37:… -
60+ Search Fund Investments: What Industries Excite Him The Most TODAY
16 september 2025 · 28 min
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). Lees meer
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.
What you’ll learn:
00:00 Intro - buy, run, and compound
02:03 Why study Tim & the origins of search funds
03:40 Tim’s path: from MBA case study to investor
05:18 60+ investments, market gets crowded, lessons learned
06:54 Flipping to buyer/operator; control & alignment
07:59 Search fund 101: traditional vs. self-funded vs. committed capital
10:54 Why search funds work: hungry operator × resilient business
12:08 First-time CEO profile: EQ is better than IQ, sales, coachability
14:28 What to buy (and avoid): the “easy to run, hard to break” box + weird niches
16:56 from LOI to close: diligence, QoE, papering the deal, seller roll/seller note
19:03 First 100 days: make payroll, listen, cadence & KPIs
20:05 Months 3-12: hire a sales leader, CRM, pipeline & talk tracks
21:56 Post-close priorities: top accounts, upgrade tools, data culture
23:03 Returns math: 4× equity without multiple expansion
24:15 Hold vs. sell; should the seller stay?
24:58 How big is the opportunity? supply/demand & off-market
26:08 Bezos vs. Musk test: singles % doubles are better than moonshots
26:53 Final advice & next steps
27:26 OutroSubscribe on Spotify:
https://open.spotify.com/show/6lr5bE3SNZF2uEE7Nb0DHh?si=cP_nAarhRmep1lvnR6uk5gSubscribe on Apple Podcasts:
https://podcasts.apple.com/us/podcast/holdco-builders/id1695713724Follow 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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How I Left PE, Bought 2 SaaS Businesses (Raising a Fund Next?) | Donza Worden Interview
12 september 2025 · 37 min
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). Lees meer
Timestamps:
00:00 Intro & who Donza is (2 platforms, Capitalpad)
00:25 The spicy tweet: “Most PE investors aren’t really investors”
00:56 Why PE ≠ investor training: incentives & slow feedback loops
02:24 Donza’s origin story: island → banking → PE
04:27 The hangar conversation that changed his life
06:05 PE associate programs, fund velocity & early reps
07:27 Investment philosophy setup (industry → company → price)
08:31 Building conviction: Five Forces, 2–4 thesis pillars, price last
10:50 What he kept/ditched from institutional PE before launching
12:02 Why 2024 to launch Clear Peak; co-founding with Luke
14:55 Model choice: independent sponsor now, fund optionality later
16:24 Deal #1: cruise/maritime maintenance software—core thesis
18:10 Capital reality on Deal #1: family offices & cold-start relationships
18:58 Deal #2: faster process; staged diligence & value-creation session
21:08 Operating the portfolio: GTM at IT Sync; financial visibility at Entara
23:55 Back to market for Deal #3; discipline on timing
24:08 Highest-ROI levers post-close (company-specific, no cookie cutter)
25:17 Choosing investors: family offices vs. SBIC; red flags
27:20 Superpower & weakness: depth of work vs. time trade-offs
29:33 Taking risk: leaving institutional PE; AI’s coming impact
31:18 Hardest skill shift: decision-making rests with you
32:16 Hours & lifestyle now vs. institutional PE
33:12 Happiness & autonomy; what “winning” (MOIC/IRR) looks like
34:18 What he’s studying now (IT services, vertical SaaS, mental models)
35:12 Practicing intellectual curiosity; inviting dissent
36:22 Favorite book: Behave (Robert Sapolsky)
37:15 Wrap-up & future check-inSubscribe on Spotify:
https://open.spotify.com/show/6lr5bE3… -
This 70/30 Model Leads to Highest Returns
10 september 2025 · 6 min
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: Lees meer
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, team energy
05:31 Deal cadence & outlook: 1–2 deals/per year; potential portfolio saleFollow 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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How I Bought 7 Businesses and Built a $34M Holding Company | Doug Lepisto Interview
8 september 2025 · 52 min
Operator-first, place-based PE done right. In this episode, Doug Lepisto (co-founder of Sleeping Giant Capital) breaks down how his team backed 7 searchers to buy 7 local companies, deploying a $34M Fund I and gearing up for Fund II. Lees meer
We unpack the full playbook—how they source in-region deals, why they bet on the operator first, and the exact 10-10-10 searcher economics.
Doug shares how they structure boards, protect the downside, and build long-term, hold-forever companies with a university-powered talent pipeline.
Timestamps:
00:00 Intro (Sleeping Giant overview: place-based, West MI, Fund I $34M)
00:33 Doug’s background
04:41 Sleeping Giant timeline
10:32 Buffett, Brent Beshore, ETA/search, university model
13:42 Fundraising journey (easiest no, institutions vs HNW/FOs, strategy)
16:13 Ideal targets (shift to higher-quality $3 to $5M EBITDA businesses)
18:14 First acquisition setup
19:29 First acquisition story
21:41 Deal size (larger than initial target)
22:05 Seller rollover & post-close roles (case by case)
23:14 Operating lessons (protect downside, boards, emotions; big deal are better than many small)
26:25 Pipeline & selectivity (LOIs as the key KPI)
28:48 Operators-first vs deal-first (why back people)
30:32 The 8-week Acquire Course (1:1 coaching format)
34:56 Course throughput & outcomes
35:57 Searcher economics (10/10/10 vesting, salary/bonus)
37:58 Portfolio update & headwinds (tariffs, organic growth systems, board design)
40:27 Fund II focus (double down on place, build an enduring machine)
42:10 Defining long-term (25-year term, durable niches like metal components)
43:38 Liquidity in a long fund
46:04 Scalability (2–3 CEOs at a time; replication in other regions)
47:29 Place-based investing philosophy & macro trends
50:51 Quickfire (best advice and favorite book)Subscribe on Spotify:
https://open.spotify.com/show/6lr5bE3SNZF2uEE7Nb0DHh?si=cP_nAarhRmep1lvnR6uk5gSubscribe on Apple Podcasts:
https://podcasts.apple.com/us/podcast/holdco-builder… -
How to Build a $30M HVAC HoldCo (4 Acquisitions and Next Goal $150M)
5 september 2025 · 44 min
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. Lees meer
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, bought better, and then built a division from scratch that hit $3.66m in year one with double-digit margins.
Today it’s five companies, ~$30m revenue, and a clear target: $150m by 2033.
This conversation is the real operator’s playbook:
- how to know when it’s time to jump,
- what to buy and why,
- the hybrid non-integration model that actually works,
- the communications cadence that calms teams and customers,
- and the unsexy habits that compound.Timestamps:
00:00 - Intro: who Sam Turner is (ex-CFO → UK SMB/HVAC acquirer)
01:12 - Why leave a high-paying CFO job for blue-collar businesses?
01:36 - Dissatisfaction: politics, travel, no autonomy, family priorities
03:10 - How he made it happen: engineered exit & planning window
04:54 - Choosing ETA/search over property (people-focused)
05:49 - Didn’t pick an industry until after starting the search
05:54 - Research approach: 15–30 sectors explored
07:52 - Acquisition criteria: large & fragmented, multiple arbitrage, non-tech
09:54 - Capital model: deal-by-deal, retain majority equity
10:43 - Strengths & weaknesses
14:04 - Timeline & where the group is today (first deal Dec 2021; 4 buys + 1 organic; ~$30m rev; 2033 target $150m)
17:31 - First acquisition story
23:39 - What he buys now: $3–12m revenue, ~10% EBITDA, commercial/built-environment
25:14 - Why buy multiple quickly: diversify operational risk
28:16 - Post-acq philosophy: no full integration; hybrid model, common tech
32:51 - Why #2 and #3 worked: better margins, owner transition, heavy communication
36:58 - Organic playbook: hire industry COO, spin up division, recruit A-players
39:33 - Organic results: ~$3.… -
Buying 500+ Businesses and Turning $100k Into $10B - Fernando De Leon of Leon Capital Group
3 september 2025 · 31 min
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. Lees meer
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
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
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 teaserSubscribe on Spotify:
https://open.spotify.com/show/6lr5bE3SNZF2uEE7Nb0DHh?si=cP_nAarhRmep1lvnR6uk5gSubscribe on Apple Podcasts:
https://podcasts.apple.com/us/podcast/holdco-builders/id1695713724Follow 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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How I Bought 20+ Small Farms and Built a $350M HoldCo in My 30s | Jack McCarthy Interview
27 augustus 2025 · 39 min
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. Lees meer
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
00:06:26 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)
00:18:10 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)----------------------------------------------
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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This Is the Best $1M EBITDA Business (A Lesson From Talking to 2,000 Business Owners)
24 augustus 2025 · 55 min
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. Lees meer
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)
00:07:49 - 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----------------------------------------------
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 dec…
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We closed 7 deals in 14 months (first $140m and a portfolio of 13 companies)
20 augustus 2025 · 54 min
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. Lees meer
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
00:05:22 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
00:17:35 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 “profession… -
Larry Gagosian Makes $1B+ a Year Brokering Off-Market Art (While Still Owning 100% Of The Business)
15 augustus 2025 · 38 min
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: Lees meer
- 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
00:08:16 - 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)
00:18:39 - 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)----------------------------------------------
Follow Mikk/PrivatEquityGuy on Twitter: https://x.com/PrivatEquityGuy
This podcast is for informational purposes only an…
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The Next Andrew Wilkinson? Building a 6-Company HoldCo (Bootstrapped with a 7-Figure Exit)
11 augustus 2025 · 1 uur 3 min
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. Lees meer
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
00:36:15 - 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----------------------------------------------
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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How Michael Ovitz and Steve Schwarzman From BlackStone Find 10s
6 augustus 2025 · 43 min
What if your next CEO hire could 10x—or destroy—your portfolio company? Lees meer
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
00:06:40 - 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
00:17:59 - 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----------------------------------------------
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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How I Bought 4 Companies After Raising Millions from 35 Investors | Danny Vivier Interview
1 augustus 2025 · 57 min
Danny Vivier is quietly building one of the most thoughtful vertical SaaS portfolios in the game. Lees meer
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
00:06:59 - 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
00:16:06 - 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----------------------------------------------
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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Follow This Private Equity Model and You'll Win (They Turned a $25K Loan Into a $15B AUM Fund)
29 juli 2025 · 47 min
In this episode of HoldCo Builders, I dive deep into the playbook of one of the most consistently high-performing investors in the world: Graham Weaver, Founder of Alpine Investors. Lees meer
Alpine isn’t just a private equity firm, it’s a human capital compounding machine that grew from a $25,000 loan to over $15B in AUM, all by betting on people. Graham didn’t win by chasing deals, he won by outbehaving everyone else in the industry.
In this deep dive, I break down:
00:00:00 - Intro: Why Study Graham Weaver
00:02:21 - Lesson 1: Your Business is a Reflection of Your Will
00:07:58 - Lesson 2: Purpose Over Strategy
00:15:21 - Lesson 3: Winnable Games
00:22:55 - Lesson 4: Talent as Alpha
00:27:19 - Lesson 5: Building Platforms Before Acquisitions
00:32:36 - Lesson 6: Managing for Long-Term Value
00:37:35 - Lesson 7: Personal Growth as Business Strategy
00:45:30 - Final Reflections and Call to Action----------------------------------------------
Subscribe on Spotify:
https://open.spotify.com/show/6lr5bE3SNZF2uEE7Nb0DHh?si=cP_nAarhRmep1lvnR6uk5gSubscribe on Apple Podcasts:
https://podcasts.apple.com/us/podcast/holdco-builders/id1695713724Follow 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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How to Build a $200M HVAC HoldCo Without Outside Capital (2 Acquisitions and Organic Growth)
25 juli 2025 · 1 uur 7 min
Today on HoldCo Builders, I’m joined by Chris Hoffman, CEO of HP Solutions Group, the $200M+ holding company behind one of America’s fastest-growing residential services brands. Chris and his brother took over their father's $9M HVAC business in 2015 and turned it into a multi-brand platform with over 600 employees — all without raising outside capital. Lees meer
Timestamps:
00:00:00 - From $9M to $150M: Why scaling gets easier
00:01:22 - The mastermind that transformed our business
00:03:56 - We didn’t invent the playbook, we executed the process playbook
00:06:54 - I almost let my ego kill our growth
00:08:19 - How we grew 35% annually for 8 years
00:10:02 - Should more entrepreneurs take part in masterminds?
00:11:37 - Why I paid myself $80K for 5 years
00:15:30 - How we built a game-changing advisory board
00:19:38 - We hired a board member as our company president
00:22:24 - Running a family business without the drama
00:25:33 - Our mission: Become the #1 private home service company
00:31:19 - Why we only do 1–2 acquisitions a year
00:33:33 - Only looking for markets with a lot of tailwinds
00:37:35 - Competing with private equity on great deals
00:42:28 - How we 2.5x’d profit at Ferguson Roofing
00:46:18 - The financing strategy that fuels our sales
00:52:49 - How we scaled with zero outside capital
00:55:51 - Capital allocation and debt terms from the banks
00:58:43 - The mindset shift to break through the $30M ceiling
01:01:34 - The goal is to just stay in the business and do the same things we’ve done so far----------------------------------------------
Subscribe on Spotify:
https://open.spotify.com/show/6lr5bE3SNZF2uEE7Nb0DHh?si=cP_nAarhRmep1lvnR6uk5gSubscribe on Apple Podcasts:
https://podcasts.apple.com/us/podcast/holdco-builders/id1695713724Follow 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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This Model Beats Private Equity Returns (30-50%+ IRR)
19 juli 2025 · 32 min
What if the key to building real wealth wasn’t in startups or VC, but in buying simple, cash-flowing businesses? Lees meer
In this episode, we dive deep into the minds of Royce Yudkoff and Rick Ruback — the Harvard professors who quietly shaped the world of search funds and acquisition entrepreneurship. Their ETA class at HBS has launched hundreds of successful HoldCos and operators.
We explore the two paths of search (funded vs. self-funded), why the multiple matters more than growth, what red flags kill deals, and how great operators build empires by holding longer.
If you’ve ever thought about buying a business — this is the playbook.
Timestamps:
00:00:00 - Intro: The Hidden Giants Behind ETA
00:01:01 - The Bifurcation of Search: Funded vs. Self-Funded
00:06:16 - The Magic Is in the Multiples, Not Growth
00:09:51 - What to Look For: 5 Filters for Great Acquisitions
00:14:54 - Red Flags That Quietly Kill Deals
00:19:01 - Where Real Growth Actually Comes From
00:21:58 - Why Great Operators Still Sell Too Early
00:25:51 - The Real Search Process (And Why It Works)
00:29:45 - More Money Than Time: The Real Reason to Buy a Business----------------------------------------------
Subscribe on Spotify:
https://open.spotify.com/show/6lr5bE3SNZF2uEE7Nb0DHh?si=cP_nAarhRmep1lvnR6uk5gSubscribe on Apple Podcasts:
https://podcasts.apple.com/us/podcast/holdco-builders/id1695713724Follow 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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How to Do 10+ Deals per Year ($8M in Revenue and $2.5M in EBITDA) | Jack Bennett
15 juli 2025 · 1 uur 7 min
Jack Bennett is the co-founder of Lighthouse Capital, a firm advising and investing in small business acquisitions across the U.S. and Canada. In just under two years, Jack and his team have closed over 20 deals, built a 10-location accounting roll-up generating $8M in revenue, and developed a unique dual structure combining M&A advisory and direct equity investments. Lees meer
In this episode, we cover:
00:00:00 - Introduction to Jack Bennett & Lighthouse Capital
00:00:47 - Building a ghostwriting agency for wealthy clients
00:07:30 - Meeting Ben Kelly and founding Lighthouse Capital
00:12:39 - Early days of Lighthouse and first hires
00:15:38 - Structure and the types of companies they invest in
00:17:25 - When do they decide to advise vs. invest
00:19:00 - Why combine M&A advisory and rollups
00:25:02 - Uniqueness of Lighthouse’s dual strategy
00:29:10 - Converting fees into equity and how it actually works
00:33:55 - Deal quality, ownership, and control
00:37:11 - Pros and cons of following the M&A and roll-up strategy at the same time
00:41:34 - Cash for equity and “see you at the first board meeting”
00:45:19 - Being the youngest on the founding team
00:48:39 - Four acquisitions and ten locations
00:52:09 - Everything post-acquisition
00:55:20 - The importance of integration
00:59:53 - What Jack believes earns him the best returns
01:03:29 - Is this the best investment advice you’ve ever heard?----------------------------------------------
Subscribe on Spotify:
https://open.spotify.com/show/6lr5bE3SNZF2uEE7Nb0DHhSubscribe on Apple Podcasts:
https://podcasts.apple.com/us/podcast/holdco-builders/id1695713724Follow Mikk/PrivatEquityGuy on Twitter: https://x.com/PrivatEquityGuy
Jack on X: https://x.com/jackentr3
This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions.
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How I Left Investment Banking to Build a Search Fund (Luca Hany from Amboro Capital)
12 juli 2025 · 58 min
Ever wonder what it takes to start a solo search fund in Europe? Luca Hany left investment banking and bet on himself to build Amboro Capital, one of the few traditional search funds in Switzerland. Lees meer
In this raw and practical episode, Luca dives into his strategy, the gaps in the Swiss market, how he raised capital with no operating experience, and how he builds deal flow from scratch in a country with no public company database.
In this episode, we cover:
00:00:00 - Intro to Luca Hany and Amboro Capital
00:00:27 - Why Luca left investment banking after 6 years
00:02:22 - Discovering ETA and building a personal mode
00:05:16 - Why Switzerland is ripe for ETA—and why no one's doing it
00:07:52 - The Swiss succession crisis in SMEs
00:11:12 - Educating SME owners on alternatives to selling to competitors
00:14:12 - Letter-based outreach strategy and surprising owner reactions
00:16:30 - Lack of company databases and why it's actually an advantage
00:18:28 - Balancing fundraising, deal sourcing, and strategy
00:20:45 - Investor objections: "Does ETA even work in Switzerland?"
00:22:34 - Addressing lack of operating experience head-on
00:24:49 - Why Luca chose to go solo and how he avoids loneliness
00:26:11 - Real costs of doing a solo search in Switzerland
00:28:54 - Recruiting and paying top-tier interns
00:31:15 - What niches and industries Luca is targeting
00:35:49 - How he defines a great business (non-obvious signs)
00:38:00 - Adding Southern Germany to the search scope
00:40:55 - Real competition in the Swiss deal landscape
00:43:04 - Typical deal structures and seller expectations
00:48:15 - When to pull the trigger on a business
00:50:15 - Red lines, long-term vision, and personal motivation
00:54:13 - Best investment advice Luca ever received
00:55:00 - Is he under pressure? Why he sees this as a privilege
00:56:10 - Favorite book and closing reflections----------------------------------------------
Subscribe on Spotify:
https://open.spotify.com/show/6l… -
How The Chainsmokers Built a $200M AUM Fund (Using 7 Proven Operating Principles)
8 juli 2025 · 53 min
Few realize Drew and Alex of The Chainsmokers are world-class operators and disciplined investors --- with over 220 portfolio companies through their investment firm, Mantis. Lees meer
In this solo deep dive, I break down the real Chainsmokers story — from sleeping on floors and running fan CRMs to building a systemized investment engine backed by General Catalyst and Mark Cuban.
Timestamps:
00:00:00 - Why This Episode Exists
00:01:54 - What Drives the Great Ones
00:05:14 - Be Bad First, Then Get Good
00:07:31 - Systems Before Scale
00:10:29 - Two Questions Every Buyer Should Ask
00:15:14 - The Chainsmokers' Investments and Product Portfolio Today
00:19:20 - If Your Revenue Doubled Overnight, Would Your Systems Survive?
00:25:33 - Build Something Only You Can Build and Acquire
00:32:25 - People Don’t Trust People They Don’t See
00:34:58 - What It Looks Like in Year 10
00:36:35 - What Makes Long-Term Investing So Powerful: Everyone Else Burns Out
00:41:16 - Build a World, Not Just a Stack of Companies
00:47:01 - Fix the “Plumbing” Before You Scale
00:52:05 - Are You Building an Investment Firm Worth Joining?----------------------------------------------
Subscribe on Spotify:
https://open.spotify.com/show/6lr5bE3SNZF2uEE7Nb0DHh?si=cP_nAarhRmep1lvnR6uk5gSubscribe on Apple Podcasts:
https://podcasts.apple.com/us/podcast/holdco-builders/id1695713724Follow Mikk/PrivatEquityGuy on Twitter: https://x.com/PrivatEquityGuy
The Chainsmokers on Twitter: https://x.com/TheChainsmokers
This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions.
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How I Bought 3 Paving Companies in 11 Months ($66M in Revenue and $7M in EBITDA) | Sam Mahmood
4 juli 2025 · 58 min
Sam Mahmood is the co-founder of Pave, a holding company rolling up businesses in one of the most overlooked, unsexy, yet wildly lucrative sectors in America - paving and line striping. In just 11 months, Sam and his team have scaled to three companies doing $66M in revenue and $7M in EBITDA. Lees meer
But Sam didn’t start in asphalt. He began in medical devices, building a national distribution and manufacturing business from scratch in his 20s. After taking chips off the table and stepping back, he went searching for his next billion-dollar opportunity. What he found? Line striping.
In this episode, we cover:
00:00:00 - Intro to Sam Mahmood and Pave
00:01:41 - From medical devices to rollups
00:05:55 - Why Sam chose the paving industry
00:10:07 - Framework for choosing the right industry
00:13:22 - How to build an all-star advisory board
00:17:15 - Raising $2.5M in 30 days from retail investors
00:23:01 - Assembling the core Pave team
00:24:26 - First acquisition: D&O Contractors
00:27:15 - The thought process behind walking away from a New York deal
00:32:30 - "Do the Work" mindset and company culture
00:34:57 - 15–20 paving companies and Sam’s creative “Pave Pod” for deal flow
00:41:05 - “Confidence is two inches wide and 10 feet deep. Fear is a mile wide and an inch deep.”
00:43:13 - Second acquisition and operational strategy
00:46:46 - Why Sam turned down a $150M private equity deal
00:51:53 - Where Pave is today and what’s next
00:53:42 - Sam's “to-WHO” list vs. traditional to-do lists
00:56:10 - Sam’s favorite book and final advice----------------------------------------------
Subscribe on Spotify:
https://open.spotify.com/show/6lr5bE3SNZF2uEE7Nb0DHhSubscribe on Apple Podcasts:
https://podcasts.apple.com/us/podcast/holdco-builders/id1695713724Follow Mikk/PrivatEquityGuy on Twitter: https://x.com/PrivatEquityGuy
Sam on Twitter: https://x.com/TheSammahmood_
This podcast is for informational purposes only and should not be relied upon as a basis for inves…
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The Next Warren Buffett? Turning $2.7m Into $650m by Buying 30+ Businesses
30 juni 2025 · 18 min
Join us for a deep dive into one of the most fascinating stories in British business. In this episode, we explore RDCP Group, a UK-based holding company that grew from a £2 million equity stake into a portfolio generating over £400 million in annual revenue—all without institutional capital. Lees meer
We unpack:
00:00:00 - Intro
00:00:49 - What makes Sameer and Iryna special as operators, investors, or builders?
00:01:57 - What surprised Alex most during his research?
00:04:12 - What are the biggest philosophical differences between building a HoldCo like RDCP versus launching a fund?
00:07:17 - How does RDCP’s financing model differ from traditional PE-backed serial acquirers?
00:10:28 - What made the care home strategy bankable, and how did they leverage it to fund other ventures?
00:13:49 - RDCP’s aspiration to become the “British Berkshire Hathaway” - realistic or PR?
00:14:30 - Does the current structure - heavily SPV-based and bank-leveraged - can evolve into a more permanent capital vehicle?
00:16:45 - What did Alex personally learn the most from this research?----------------------------------------------
Subscribe on Spotify:
https://open.spotify.com/show/6lr5bE3SNZF2uEE7Nb0DHhSubscribe on Apple Podcasts:
https://podcasts.apple.com/us/podcast/holdco-builders/id1695713724Follow 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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How I Bought 7 Small Businesses and Had One Exit That Returned a 35x MOIC | Dev Shah Interview
27 juni 2025 · 1 uur 17 min
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. Lees meer
In this episode, we cover:
00:00:00 - Intro
00:01:56 - Discovering acquire.com and the first acquisition
00:03:04 - Overview of Pocket Fund's portfolio and team structure
00:10:08 - Building and managing a team in India to run the portfolio
00:11:03 - How he finds operators and builds systems to scale to 20+ companies
00:17:14 - His buying criteria and approach to value creation
00:21:52 - Deal sourcing
00:36:55 - Deep dive into his 35x MOIC case study (Sourcely.ai)
00:43:47 - How does Dev manage a portfolio of six companies
00:47:56 - Why he is rejecting VC and fund money for now
01:00:37 - Long-term vision and building a new Constellation-like model in India
01:05:24 - Hiring global talent----------------------------------------------
Subscribe on Spotify:
https://open.spotify.com/show/6lr5bE3SNZF2uEE7Nb0DHhSubscribe on Apple Podcasts:
https://podcasts.apple.com/us/podcast/holdco-builders/id1695713724Follow Mikk/PrivatEquityGuy on Twitter: https://x.com/PrivatEquityGuy
Dev on Twitter: https://x.com/devlikesbizness
This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions.
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How I Left BlackRock to Build 3 Companies (Then Sold Two in 5 Years) | Jamal Muse Interview
25 juni 2025 · 47 min
I sit down with Jamal Muse, a former math teacher and former Blackrock analytics professional who reinvented himself as a serial founder. He’s built and sold two brands (one for 7 figures) and is now sellling his third. Lees meer
If you're building with an exit in mind — or want to learn how top operators structure their businesses to sell — this episode is a must-listen.
📧 Interested in buying Jamal’s current business? Reach out at: mikk at privatequityguy dot com
🔔 Don’t forget to subscribe for more interviews with operators, acquirers, and builders.We cover:
00:00:00 - Intro - Meet Jamal Muse, 3-time founder with one 7-figure exit
00:01:07 - Why 50% of your earnings come at the exit, not during operations
00:03:31 - How Jamal learned to treat his business as an asset, not a baby
00:06:50 - The mindset shift behind picking the right buyer (and rejecting offers)
00:09:00 - Should you sell your business? Jamal’s take on emotional attachment
00:11:01 - Reinventing yourself: From teacher to entrepreneur to what’s next
00:19:00 - Why going public with his story was scarier than skydiving
00:22:30 - Jamal’s 3-year roadmap to build, grow, and exit a brand
00:27:00 - Common mistakes that kill exits: bad books, weak niche, messy ops
00:30:00 - Revenue vs. profit - what actually matters when selling
00:33:00 - What real buyers look for in a business (and red flags to avoid)
00:36:40 - You can dictate price or terms - but not both----------------------------------------------
Subscribe on Spotify:
https://open.spotify.com/show/6lr5bE3SNZF2uEE7Nb0DHhSubscribe on Apple Podcasts:
https://podcasts.apple.com/us/podcast/holdco-builders/id1695713724Follow 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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40% CAGR for Over 15 Years: UK’s Most Profitable Roll-Up?
23 juni 2025 · 18 min
True Potential has quietly compounded at 40% CAGR for over 15 years, becoming the UK's largest private equity-backed wealth management consolidator. In this deep-dive episode, we unpack the strategy behind this incredible growth story with Alex from RollUp Europe, who authored one of the most detailed research pieces on True Potential.
Learn how True Potential: Lees meer00:00:00 - Compounding at 40% for 15 years
00:00:42 - What is an IFA and why true potential stands out
00:01:33 - $500k EBITDA per employee: the aha moment
00:02:56 - How true potential earns 70–80% EBITDA margins
00:05:26 - Why 90% of AUM is in in-house funds, and why that matters
00:06:50 - True potential’s small ticket M&A machine
00:08:53 - How they avoided legal liability while acquiring clients
00:10:07 - Regulatory risks of vertical integration in the UK
00:12:18 - The hidden cost of selling to consumers (vs B2B)
00:14:40 - Why Cinven paid 20x EBITDA, and still won
00:16:01 - 3 key lessons from true potential’s buy-and-build success----------------------------------------------
Subscribe on Spotify:
https://open.spotify.com/show/6lr5bE3SNZF2uEE7Nb0DHhSubscribe on Apple Podcasts:
https://podcasts.apple.com/us/podcast/holdco-builders/id1695713724Follow Mikk/PrivatEquityGuy on Twitter: https://x.com/PrivatEquityGuy
Alex from RollUp Europe: https://rollupeurope.beehiiv.com/
This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions.
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How I Left Real Estate PE, Bought 6 Companies and Sold To A Strategic Buyer In 23 Months
20 juni 2025 · 55 min
Mike Botkin went from being a real estate private equity COO to buying a small landscaping business doing $780K in revenue - with no prior experience and no money down. Just 23 months later, he sold it for millions after scaling through 6 smart acquisitions and ruthless focus. Lees meer
This is one of the most tactical and inspiring HoldCo journeys you’ll hear in a long time. If you’ve ever thought about leaving your job to buy a business, this is the episode that might make you do it.
In this episode, we cover:
00:00:00 - Why Mike left a PE COO role to buy a $780K landscaping business
00:00:31 - “I wasn’t qualified” - Mike explains why he took the leap anyway
00:04:30 - Burn the boats: betting everything on himself with a newborn at home
00:06:23 - How he found his first business on BizBuySell and closed in 45 days
00:08:20 - The myth of perfect deals and how Mike created his own luck00:14:10 - Why Mike fired $3M in revenue and focused only on profitable customers
00:20:12 - A reporting hack that boosted margins by cutting wasted labor time
00:22:53 - He wasn’t buying businesses, he was acquiring great people
00:26:10 - Don’t buy from tired sellers, look for mid-career owners instead
00:28:20 - Why Mike avoided SBA loans and bought 6 businesses with no debt
00:34:19 - How he raised millions without putting in a dollar of his own
00:38:55 - The exit: selling the company and why early retirement didn’t stick
00:42:50 - Starting Canvas Outdoors: replicating the model with two platforms
00:44:15 - Why maniacal focus beats portfolio diversification for HoldCos
00:50:00 - Lessons from a CEO: “Keep the main thing the main thing"
00:52:42 - Mike’s favorite book and his brutally honest best investment advice----------------------------------------------
Subscribe on Spotify:
https://open.spotify.com/show/6lr5bE3SNZF2uEE7Nb0DHhSubscribe on Apple Podcasts:
https://podcasts.apple.com/us/podcast/holdco-builders/id1695713724Follow Mikk/PrivatEquityGuy on Twitter: https://x.com/P…
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How To Raise $159M, Acquire 6 YouTube Channels and Sell To Blackstone For $3B in 3.5 Years
16 juni 2025 · 24 min
The $3 Billion Rollup: Inside Moonbug’s Epic Exit (with Alex Prokofjev from Rollup Europe) Lees meer
What do Cocomelon, Blippi, and Little Baby Bum have in common? They were all part of one of the most impressive media rollups in history: Moonbug Entertainment — a business that scaled from 0 to $100M EBITDA in under four years and exited for $3 billion to Candle Media (backed by Blackstone).
In this episode, I sit down with Alex Prokofjev, co-founder of Rollup Europe, who did a deep dive into Moonbug’s strategy. We unpack the insane deal-making, content flywheel, multi-channel monetization, and the unique cap table structure that fueled this rocketship.
We explore:
00:00:00 - Intro: The Most Fascinating Exit in Modern Media?
00:00:42 - Why Moonbug Was a Contrarian Bet in 2018
00:02:15 - Meet the Dream Team: Disney + Wildbrain + M&A
00:03:35 - How They Scaled to $3B in Just 3.5 Years
00:05:00 - Moonbug’s Playbook: Monetizing Kids' IP Across Channels
00:06:15 - Cap Table Deep Dive: 6 Share Classes & Incentive Design
00:07:30 - How Moonbug Achieved 50% EBITDA Margins Across 30 Brands
00:09:00 - Little Baby Bum: The $90M Deal That Changed Everything
00:13:00 - Moonbug’s Exit to Candle Media: Was $3B Worth It?
00:16:00 - Why Moonbug Hasn’t Been Copied (Successfully)
00:17:20 - The Legal Battles & Risks Behind the Scenes
00:19:35 - Founders’ Payday: Who Made How Much in the Exit?
00:20:30 - Top 3 Lessons for Today’s Rollup Operators----------------------------------------------
Subscribe on Spotify:
https://open.spotify.com/show/6lr5bE3SNZF2uEE7Nb0DHhSubscribe on Apple Podcasts:
https://podcasts.apple.com/us/podcast/holdco-builders/id1695713724Follow Mikk/PrivatEquityGuy on Twitter: https://x.com/PrivatEquityGuy
Alex from RollUp Europe: https://rollupeurope.beehiiv.com/
This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions.
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How They Invest in 6-8 Boring, Owner-Operated Businesses Each Month | Judd Goodrich interview
13 juni 2025 · 1 uur
In this episode of HoldCo Builders, I sit down with Jude Goodrick, Head of Capital Markets at Mainshares—a fast-growing platform that's quietly reshaping small business acquisitions. Lees meer
Mainshares helps acquisition entrepreneurs find the capital they need to buy real, cash-flowing businesses. Jude has seen hundreds of deals and works directly with operators and investors to get them across the finish line.
In This Episode We Discuss:
00:00:00 - Intro: Why Jude Goodrick is at the center of SMB acquisitions
00:00:42 - Jude's background and journey from Carta to Mainshares
00:01:36 - The origin story of Mainshares and what problem it solves
00:03:09 - Solving the chicken-and-egg problem of deals vs. capital
00:06:47 - Feedback from having 800 conversations with operators
00:07:59 - First acquisition took about a year
00:08:48 - How Mainshares makes money and structures deals
00:17:31 - A common reason operators come to them
00:19:47 - Why Mainshares isn't building a traditional PE firm
00:23:32 - Could Mainshares build a permanent HoldCo?
00:24:58 - Investor experience on the Mainshares platform
00:32:12 - What happens when a deal is oversubscribed?
00:36:10 - Post-acquisition support: credit lines, equipment loans
00:38:21 - Who are the operators? First-timers vs. seasoned pros
00:40:35 - MBA vs. blue-collar operators: who performs better?
00:43:17 - What happens when things go wrong post-acquisition?
00:45:00 - Structuring preferred equity and step-ups
00:48:40 - Jude’s advice to aspiring acquisition entrepreneurs
00:51:35 - What separates great operators from average ones
00:57:29 - What Jude enjoys most - and least - about his role
00:59:20 - Would Jude ever buy a business himself?----------------------------------------------
Subscribe on Spotify:
https://open.spotify.com/show/6lr5bE3SNZF2uEE7Nb0DHhSubscribe on Apple Podcasts:
https://podcasts.apple.com/us/podcast/holdco-builders/id1695713724Follow Mikk/PrivatEquityGuy on Twitter: https://x.com/PrivatEquity…
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How Plumbing and HVAC Investors Turned $500K Into $6 Billion Exit
10 juni 2025 · 18 min
Is this the most underappreciated rollup in Europe? Lees meer
In this episode, we dive deep into HomeServe — the unsexy plumbing and HVAC company that quietly evolved into a $2B revenue giant and was eventually acquired by Brookfield for $6B. But this isn't just a story about boilers and leaky taps.
Joining us is Alex Prokofjev, co-founder of RollUp Europe.
Whether you're an operator, investor, or aspiring acquisition entrepreneur, this episode is packed with strategic insights on rollups, recurring revenue, and scaling services with a subscription twist.
We explore:
00:00:00 - The most underappreciated Rollup in Europe?
00:00:51 - How HomeServe evolved into a vertically integrated insurance broker
00:01:45 - The business model failed not once but twice
00:03:31 - Two powerful lessons for pperators: Fintech revenue and iterating beyond your first idea
00:04:40 - Great timing
00:05:57 - Why HVAC became HomeServe’s rollup goldmine: high-trust, high-margin, mission-critical customer moments
00:08:40 - Buying small businesses with attractive multiples
00:07:15 - How HomeServe Justified Higher Acquisition Multiples
00:10:04 - Why public market investor give up on HomeServe
00:12:40 - The Brookfield playbook Post-Acquisition: Breaking up the business and doubling down on HVAC rollups in Europe
00:14:03 - Biggest takeaway: Be ready to pivot your entire business
00:15:15 - Running a mission critical requrring revenue business
00:16:26 - Similar strategies on different verticals----------------------------------------------
Subscribe on Spotify:
https://open.spotify.com/show/6lr5bE3SNZF2uEE7Nb0DHhSubscribe on Apple Podcasts:
https://podcasts.apple.com/us/podcast/holdco-builders/id1695713724Follow Mikk/PrivateEquityGuy on Twitter: https://x.com/PrivatEquityGuy
Alex from RollUp Europe: https://rollupeurope.beehiiv.com/
This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions.