Buyers and Builders

Christopher Hillier is a seasoned entrepreneur with over 15 years of experience in the employee benefits industry.

He began his journey as the Co-Founder and President of Benefit Health Advisor, a full-service employee benefits brokerage based in Englewood, Colorado.

In our conversation, we delve into Chris’s entrepreneurial journey, from starting a brokerage firm from scratch and scaling it to $16M in top-line revenue, to acquiring an insurance underwriting company on the verge of collapse and turning it around for a strategic exit.

We also explore his insights on the ETA (Entrepreneurship Through Acquisition) space, where he is now a recognized expert, and his perspective on time management—an area he’s written a book about.

Chris shares lessons learned from navigating acquisitions, growing businesses, and managing teams, as well as his thoughts on the future of employee benefits and wellness in a rapidly evolving marketplace.

Please enjoy this conversation with Christopher Hillier, serial entrepreneur, investor and educator in the ETA space.

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Timestamps:

00:00:00 - Intro

00:00:45 - Christopher's story before founding, building and buying the company

00:04:35 - How does the company make money?

00:10:53 - Landing the first major clients

00:16:55 - First acquisition, buying distressed assets

00:20:49 - The reason for selling the company to a strategic buyer

00:24:11 - It's all harder than you'd ever imagine

00:30:08 - A perfect timing to sell a business: cash, stock, earn-out

00:34:10 - The importance of a right fit between buyer and seller

00:38:40 - Investing in search funds (love for ETA - entrepreneurship-through-acquisition)

00:43:09 - Buying an already established business is a kind of miracle

00:48:19 - The search process to find the right opportunity takes a long time and its lonely

00:56:21 - Chasing money

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Follow Mikk/PrivatEquityGuy on Twitter: https://x.com/PrivatEquityGuy

Christopher on LinkedIn: https://www.linkedin.com/in/christopher-hillier-88621113/

This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions.

Santino DeFranco is a former UFC fighter turned entrepreneur who has successfully transitioned from the octagon to the world of business ownership. Santino has acquired two companies: a Shell Gas Station with a Krispy Krunchy Chicken franchise and a restaurant hood cleaning business. In this episode, we dive into his journey from professional fighting to becoming a business owner, exploring how his competitive mindset and resilience have shaped his approach to entrepreneurship.

Santino is also a highly sought-after MMA coach who has trained and guided world champions in the UFC, bringing the same level of discipline and strategy to coaching as he does to running his businesses. We discuss what it takes to operate across such diverse industries, his insights into finding value in small businesses, and the lessons he's learned along the way.

Please enjoy this conversation with Santino DeFranco—fighter, coach, and entrepreneur.

Enjoy the episode? Make sure you SUBSCRIBE for more.

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Timestamps:

00:00:00 - Introduction

00:00:56 - Santino and his wild life as a UFC fighter before his first acquisition

00:02:15 - Creation of the first iPhone and Android app called Ultimate MMA

00:03:29 - Injuries and life as an MMA trainer for UFC fighters

00:04:21 - I started looking for companies to buy

00:05:21 - What sites does Santino use to find businesses

00:07:08 - Find the first business to buy - a gas station

00:07:42 - Where does Santino's entrepreneurial gene come from?

00:10:02 - Tough decision: go back to work or start and build different companies

00:10:58 - Most of the fighters ended up going broke, so Santino pushes them to invest and acquire the company

00:13:35 - Why he is bullish on buying companies

00:15:34 - Financial situation before buying the first company

00:17:41 - Details of the first acquisition

00:19:45 - You don't have to be a member of Mensa to do this job

00:21:00 - Advisors on the first transaction

00:23:01 - Negotiations with the owner

00:26:25 - Doing due diligence all by himself

00:29:10 - Reinvesting all profits into the company

00:32:10 - First big mistake post-acquisition

00:35:45 - Why he loves the gas station business

00:38:44 - 2nd acquisition

00:42:19 - Companies Santino prefers to buy

00:45:52 - The reason why the seller sold the company

00:48:54 - How he found this deal

00:51:31 - Financial situation before the second acquisition

00:56:27 - Hiring great people and taking care of employees by giving them a raise

00:58:17 - When is the right time to acquire company number 3

01:01:19 - Working with children and thinking about buying an 8-figure business

01:06:07 - "If someone else can do it, you can do it"

01:10:49 - Who does Santino learn from, what books does he listen to

01:15:21 - How Santino manages it all: family, businesses, coaching, reading, podcast

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Follow Mikk/PrivatEquityGuy on Twitter: https://x.com/PrivatEquityGuy

Santino on Twitter: https://x.com/TinoDeFranco

This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions.

Meet Joe Van Deman and Colin King

Founders of Circle City Capital Group. Starting with a small amount of savings and an SBA loan, over the past six years, they’ve made 14 acquisitions that have been consolidated into 4 companies, employing a total of 200 people.

A combined $30m of revenue.

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Timestamps:

00:00:00 - Intro

00:00:55 - How Joe and Colin met and what they did before their first acquisition

00:07.32 - Quitting their jobs to start a 50/50 partnership with a "stranger"

00:12:29 - First acquisition

00:20:33 - Second acquisition

00:24:45 - The industries and companies they are looking at

00:32:55 - Current portfolio and deals made so far

00:41:42 - How they manage a portfolio of 10+ companies

00:49:31 - How they survived the hard times

00:57:13 - Post acquisition and learning the specifics of the industry/field within 90 days

00:59:44 - Salary, paying dividends or reinvesting the profits

01:01:05 - Thoughts on the next acquisitions

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Follow Mikk/PrivatEquityGuy on Twitter: https://x.com/PrivatEquityGuy

Colin on Twitter: https://x.com/valuedontlie

Joe on LinkedIn: https://www.linkedin.com/in/joevandeman/

This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions.

Jason Andrew is the co-founder of a holding company Arbor Permanent Owners - team of operators and investors committed to growing businesses for the long-term.

They just closed their fundraise and cornerstone deal: 40-year-old manufacturing business in the materials handling sector. $25m in revenue, 25%+ EBITDA

Jason, Simon and Rowan have done an exceptional job in their first year at Arbor Permanent Owners

Their structure, strategy, fundraising, and first acquisition are all unique—and we cover each.

Timestamps:

00:00:00 - Intro

00:00:32 - Life before acquiring "boring" traditional businesses

00:07:15 - An honest opinion (criticism) towards search funds

00:10:52 - The best structured cold email lead to business partnership

00:14:27 - The first 30-60-90 day action plan for finding the best deals

00:23:13 - Closing the first $25 million deal in 6 months

00:32:14 - The structure of the first acquisition

00:35:50 - Feedback from investors (changing the structure of the holding company 4 times)

00:44:36 - Investor exit strategy

00:55:35 - Growing holding company from 7-fig EBITDA to $45M without raising additional equity

00:57:25 - Thoughts on never acquiring companies with less than $3mm EBITDA

01:02:59 - What does Jason consume to learn the necessary skills to double the business?

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Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/holdco-builders/id1695713724

Follow Mikk/PrivatEquityGuy on Twitter: https://x.com/PrivatEquityGuy

Jason on Linkedin: https://www.linkedin.com/in/jason-andrew/?originalSubdomain=au

This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions.

Meet ​Iryna Dubylovska and Sameer Rizvi.

Founders of RD Capital Partners (RDCP). Over the past eight years, they’ve made 31 investments that have been consolidated into 12 companies, employing a total of 2,000 people.

A combined $400m of revenue and $40m of EBITDA.

1. We pick sectors and businesses where profits and cash-flow are the main driver of value.

2. Decentralize your operations, 'Hire very smart people and leave them alone, let them get on with it.'

3. We ran companies nice and lean. We just reinvest those profits so rather leaving those profits to pay down debt quickly or for the improvement of our lifestyle.

This is how they’ve been able to compound at almost a TRIPLE digit internal rate of return (91.4% IRR) for eight years.

4. When it comes to wealth creation point of view:

Private market is better than public markets.

Because there is significantly less arbitrage…

5. At the end of the day, it's all about how you can buy $10 million for $3 million.

6. 50% industrials, 25% healthcare, 25% consumer – that’s quite a balanced portfolio in sectors and businesses which are relatively critical to the British economy.

***

A true buy and hold strategy experts.

Acquiring manufacturing, construction, engineering and healthcare companies for 3x EBITDA to sell them (if they want to) for 8-10x EBITDA.

I hope you enjoy listening.

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Timestamps:

00:00:00 - Intro

00:02:31 - Life before the first acquisition and the risk of not starting your own investment company

00:07:21 - Leaving the job and going all-in finding the 1st deal

00:09:43 - Details and the structure of the first acquisition

00:14:22 - Improving lifestyle with every transactions

00:16:04 - Overview of the portfolio and thought process behind previous investment decisions

00:23:30 - Building dealflow and finding the best deals

00:29:42 - Only buying businesses they really understand. No complex transactions.

00:34:39 - Why did they give up buying distressed companies?

00:42:41 - 12+ portfolio companies, 4 kids - how they manage it all

00:46:22 - Common reasons portco CEOs approach Iryna and Sameer

00:50:07 - Saying ‘no’ to outside capital

00:54:36 - Why don’t more people do it?

01:04:44 - How they’ve been able to do this without giving up equity

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Follow Mikk/PrivatEquityGuy on Twitter: https://x.com/PrivatEquityGuy

Sameer on Twitter: https://x.com/sameer_rdcp

This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions.

12 ideas and observations from the 56-minute conversation with Andrew Wilkinson, the the founder of Tiny, on building a 30+ business holding company:

1. Starting companies is fun, but anyone who has done it knows it is a lot of work. Buying established businesses with existing cash flow isn’t as sexy so I suspect it is wildly underrated as a way of building wealth.
2. He will occasionally pay 10x for an amazing business, but that is rare.
3. Some CEOs will go 6 months or more without speaking with Andrew.
4. Portfolio companies are not at all connected. They each operate independently.
5. Cash is kept in the company based on historical working capital needs and any extra goes to the head office for new acquisitions.
6. Andrew is willing to pay up and hire CEOs that have managed similar businesses at larger scales already before instead of trying to find underpriced less-experienced talent.
7. They have a 60-70% success rate on hiring CEOs.
8. Favorite interview question "What's the worst job you've ever had?" He finds that people that haven't had crappy jobs are less motivated.
9. Incentives act as a magnet to get what you want done.
10. Money is more meaningful to new CEOs than to founders that have been making great money for the last 5 years.
11. The first CEO he hired was paid $250k base + a couple hundred thousand variable.
12. Andrew’s strengths are: Laser focused on problems for a short period of time. Moves fast; Very good at 0 to 1. Burns bright for 15 days; Inch deep and a mile wide; Not good at execution or day to day details.

All of these highlights come from an interview with Andrew, founder of Tiny and the research I did on him.

Listening to this episode is the easiest way to download Andrew’s ideas into your brain. I hope you enjoy.

Show notes:

00:00:00 - Intro

00:00:19 - Ruthless and money focused Andrew on his early 20s

00:05:42 - 1st business, billing in USD while living in Canada

00:08:37 - First realization that it is better to buy a company compared to starting it

00:10:28 - Buying the very first business for 3x ARR and $1.5M cash

00:13:25 - Looking at companies that make a whopping $100 million in revenue but very little profit

00:19:25 - Having extreme patience while waiting for excellent companies

00:23:23 - Inefficient market and what many investors don’t understand

00:27:32 - Everything post-acquisition and delegation

00:33:45 - Andrew’s strengths and weaknesses in managing Tiny Group

00:39:04 - A huge lesson about tech businesses: small $500k businesses get big

00:43:52 - Big mistakes in pricing a product/service

00:48:20 - Lessons from Jason Fried, Sam Parr and Sahil Bloom

00:52:31 - Equity is forever. Never just give it away

Follow Mikk/PrivatEquityGuy on Twitter: https://x.com/PrivatEquityGuy⁠⁠⁠

Andrew on Twitter: ⁠⁠⁠https://x.com/awilkinson

This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions.

Selling the very first flooring business for $30k turned into a career of starting, buying and selling B2B, B2C service businesses.

A total of 6 different companies in different industries:

• 2 residential flooring companies
• 2 commercial flooring companies
• 1 restoration company
• 1 commercial cleaning company

My conversation with Robert Lombardi, the founder of Lombardi Group.

He’s sharing a journey of making plenty of mistakes and falling on his face MORE than anyone would like to admit (and this being a major part of the journey and something he’s STILL grateful for).

Enjoy.

Show notes:

00:00:00 - Intro

00:00:19 - Early days and making first $50,000

00:06:03 - Building a flooring business, targeting commercial clients vs B2C

00:20:09 - In the flooring business, B2C is good, but B2B is much better

00:22:33 - There is no recurring revenue in the floor covering business

00:31:56 - Structure in buying and investing in companies

00:37:29 - Sale of two companies at the same time

00:43:49 - Didn't know about the roll up strategy 3-4 years ago

00:53:59 - Earn trust by giving away free business leads

01:03:37 - A restoration company, a roofing company and 2 plumbing companies will be bought next

Follow Mikk/PrivatEquityGuy on Twitter: https://x.com/PrivatEquityGuy⁠⁠⁠

Robert on Twitter: ⁠⁠⁠https://x.com/roblmakeithappe

This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions.

Forget HVAC and trade businesses…

Private equity comes after your kids swim schools…

Meet Josh Scott (with wife Annie):

• 5 locations
• 7 figures in revenue (30-35% margins)
• Spends a lot of time with family and children.

Again, the riches (both time and $$$) are in niches.

We discussed:

- Raising prices and selling it to private equity (which they choose not to do now).

- Buying more and more swimming pools (property)

- Why aren't $1mm+ EBITDA deals coming to market?

- The cost of building swimming pools

- Why is selling pool fences going to be a very big business?

- A 33% IRR and spending time with the kids

Here is my conversation with Josh Scott, co-founder of SwimSRQ and Swim Academy.

Show notes:

00:00:00 - Intro

00:00:18 - Being more interested in business than just coaching

00:02:26 - Chasing a $300,000 salary vs becoming an entrepreneur

00:04:56 - Started in summer 2018; "A year later, we knew we had something..."

00:09:01 - Learning business

00:11:36 - Growth in number and decision to buy the first property

00:14:28 - Revenue streams

00:22:47 - Buying more and more swimming pools (real estate)

00:26:23 - The future is about following a boutique model (add gymnastics and ninja model)

00:30:05 - Swimming schools and private equity

00:43:17 - Competition of talent and coaches

00:44:20 - Opportunity in NYC (lots of people, no water)

00:47:03 - Technology and automation in the swimming business

00:52:31 - Expanding into the pool fence industry

Follow Mikk/PrivatEquityGuy on Twitter: https://x.com/PrivatEquityGuy⁠⁠⁠

Josh on Twitter: ⁠⁠⁠https://x.com/swimschoolJosh

This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions.

“Selling B2B SaaS is great, but owning assets is better - that's why I went and built Skaling Ventures on my own.”

A portfolio of profitable niche vertical B2B SaaS businesses:

• $1-3M with some ARR growth (~10%)
• logo retention greater than 95%
• limited go-to-market (GTM) knowledge/investment,
• fragmented competition,
• and technical founders.

We discussed how he found the best deal among the 300 deals he looked at.

How he structures deals and what his game plan is 90 days after the acquisition.

How 75% of private equity buyouts are add-ons – and how he does the same.

And much more.

I hope you enjoy listening as much as I enjoyed chatting with Kjael Skaalerud of Skaling Ventures.

Show notes:

00:00:00 - Intro

00:00:19 - Life as a B2B Saas salesman (strategy: go-to-market)

00:04:31 - Selling software to fund managers

00:09:30 - SaaS, Venture capital - The importance of game selection

00:16:25 - Where was Kjael financially before acquiring the 1st company

00:18:20 - Details on first acquisition

00:23:15 - Structure of the first transaction and Skaling Ventures Holdco

00:25:30 - Lessons learned after the first 18 months as a holdco builder

00:32:45 - First 90 days after acquisition

00:40:53 - Buying and building a business - has it been more painful/harder than he thought

00:42:15 - 75% of PE buyouts are add-ons – “we do the same”

00:47:40 - 5-year holding and reinvestment for growth

00:49:52 - Acquisition number two (under LOI)

00:53:41 - Ways to get better at what you do and build

Follow Mikk/PrivatEquityGuy on Twitter: https://x.com/PrivatEquityGuy⁠⁠⁠

Kjael on Twitter: ⁠⁠⁠https://x.com/skaalywag

Kjael's Substack: https://skalingventures.substack.com/ 

This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions.

This gentleman and his grocery store holdco opened 32 new stores in 90 days.

Tomasz Biernacki - a true capital allocator has cracked the code on how to compound his wealth (at a staggering rate!)

His grocery holding company has invested 96% of its earnings for the past 10 years.

He opened 167 new stores in Q1-Q3 in 2024.

Every store he opens returns 20-30% on invested capital…

All while net debt to EBITDA sitting at a conservative 1.1x

Wild!

There must be something special about Tomasz.

I got curious so I spent almost 6 hours reading about him (best 6 hours I've spent in a long time).

I hope you enjoy this 27-minute episode of the HoldCo Builders research edition I did on Tomasz Biernacki of Dino Polska.

Show notes:

00:00:00 - Intro

00:03:51 - Grocery store holding company

00:06:54 - Extreme discipline on net debt

00:09.01 - Real estate ownership

00:13:41 - Focus on small towns with a population of 30,000

00:18:11 - Own production of your highest margin products

00:19:22 - No money spent on ads and marketing

00:21:46 - Offer a simple product to simple small town people

00:25:34 - Reinvesting earnings rather than paying dividends

👉 Follow host 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.