I spoke with Dave Gilbert, a holding company operator who bought two different businesses over the last two years with his partner. First they bought an accounting service for $2.8 million (Note: $3.8m was mentioned during the episode, but $2.8m is the correct figure). Dave walks us through some of the legal considerations of a non-accountant buying an accounting business, including how he expanded the services. Despite all the chaos that comes in the first year of buying a business, Dave and his partner managed to grow the business by 10%. 

They also bought an engineering firm last year, and are working on finding new acquisitions. If you're interested in starting a holding company, listen to Dave's thoughtful approach to structuring deals and operating his businesses.

Thanks to Vesto for sponsoring today's episode. Visit https://vesto.com/sieva to check them out.

1:01 Starting a holding company and buying 2 businesses
3:20 A word from Vesto
4:26 Dave's previous business & exit
13:23 Buying an accounting business
24:48 Structure of the deal 
33:26 How to grow a business post-close
40:10 Buying the second business

Connect with Sieva:

X: https://sievakozinsky.com
LinkedIn:  https://www.linkedin.com/in/skozinsky/
Newsletter: https://www.sievakozinsky.com/

Connect with Dave:

X: https://x.com/dave__gilbert

Website: https://proven.co/

Want to hire top global talent? Get started with Somewhere (I'm a customer & investor) - https://hirewith.somewhere.com/sieva

Gary Hoover knows more about American Business History than anyone else. He collected over 70,000 books, about half of which were business related, and studied each of them. Gary is a walking encyclopedia when it comes to business history. His expertise and passion is retailing, and he was at the center of the retail universe for most his careers. He'll talk about how he started a book retail chain that got acquired by Barnes & Noble, and his careers at several other prominent retail chains.

I could have listened to these stories for 8+ hours, but you'll have to make do with a little less than 2 hours worth of content. 

Watch this interview if you are interested in business, how great companies came to be, and why others failed.

Highlights:

0:00 Introductions
9:57 Getting into the book business
23:47 Sam Walton & what makes a great CEO
29:32 Dying retail businesses 
37:41 The art of building great malls
41:12 What would Gary work on today?
46:58 History of conglomerates and holding companies
1:09:33 Antitrust and monopolies
1:27:02 Gary's 70,000 book collection (and how he lost it)

Connect with Sieva:

X: https://sievakozinsky.com
LinkedIn:  https://www.linkedin.com/in/skozinsky/
Newsletter: https://www.sievakozinsky.com/

Connect with Gary:

Website: https://americanbusinesshistory.org/


Want to hire top global talent? Get started with Somewhere (I'm a customer & investor) - https://hirewith.somewhere.com/sieva

 I sit down with Founder & CEO of Vesto, Benjamin Doepfner, a service we use at Enduring Ventures. We had a huge problem: Our controller had to spend hours logging into dozens of bank portals just to get the cash balances across several accounts for our 25+ businesses.

That time could have been much better spent. That's where Vesto comes in. They give you all of your company's financial accounts in one view. Vesto connects all of our banks into one simple dashboard. With real-time balances, transactions, and cash flow monitoring – we went from dozens of account logins to one.

Learn more here: https://www.vesto.com/sieva (Tell them I sent you)

Thank you to Vesto for sponsoring the Business Buying Academy. 

I chatted with Brian Wolfe, an expert on M&A from all levels - he worked as a partner at a big law firm for 17 years, helping to close huge deals. Now he's in the world of ETA (entrepreneurship through acquisition). He helps searchers get started, and he's bought some businesses himself - including a rollup of marketing SaaS businesses. Brian gives a masterclass on buying businesses.

Highlights:

0:58 Going from lawyer to investor
9:25 Rolling up marketing software businesses
19:33 Selling the rollup
26:51 Earnouts in M&A (good or bad idea?)
33:18 Multiple expansion is the 8th wonder of the world
36:43 Personal guarantees
42:20 Sieva's first deals
44:12 Brian's current business, Funded Ventures

Connect with Sieva:

X: https://x.com/sievakozinsky
LinkedIn:   https://linkedin.com/in/skozinsky 
Newsletter: https://sievakozinsky.com

Connect with Brian

LinkedIn:   https://linkedin.com/in/brianwolfe
Website: https://fundedventures.com

Want to hire top global talent? Get started with Somewhere (I'm a customer & investor) - https://hirewith.somewhere.com/sieva

I chatted with Jeremy Yamaguchi, an entrepreneur who's built many empires in home services: with home cleaning first, then lawncare, and now pool services. We talk about the economics of the home service business models he's worked in, how he acquires pool service companies, and how he's scaled to over $100 million in GMV. Watch this video if you want to build a home service empire. And if you're selling a pool company, contact Jeremy through his website cabanapools.com

0:35 Why Jeremy loves home service businesses
4:35 Growing the lawn care marketplace
7:40 How to grow home service businesses
16:54 AI in home services
18:31 Buying pool companies
23:50 Different home service verticals
28:02 Raising VC money
31:49 How much is a pool business worth?


Connect with Sieva:

X: https://x.com/sievakozinsky
Newsletter: https://sievakozinsky.com

Connect with Jeremy:

X: https://x.com/jeremyyamaguchi
Website:  https://cabanapools.com

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Want to hire top global talent? Get started with Somewhere (I'm a customer & investor) - https://hirewith.somewhere.com/sieva

Today I sit down with Chris Edwards, who bought a flooring business in Steamboat Springs, Colorado. He bought the business for $1.7 million, grew revenue by 50%, and doubled SDE (seller discretionary earnings). He then exited the business after about 3 years, earning himself a 24X return on his invested capital (most of the deal was financed with SBA debt, so he was able to make a large return on his down payment).

Highlights:

5:19 Getting into ETA
7:17 Chris' search criteria
9:54 How long did the search take?
13:56 Process of buying the business
17:04 Structure of the deal
20:21 How he improved the business
22:50 First 6 months was a knife fight
27:30 Why deals go bad
34:15 Exiting the business


Connect with Sieva:

X: https://x.com/sievakozinsky
LinkedIn:   / skozinsky  
Newsletter: https://sievakozinsky.com

Connect with Chris:

X: https://x.com/toph_edwards
LinkedIn: https://www.linkedin.com/in/chris-edwards-44664052

Esteban Reyes talks with me about how he's built and sold 3 companies, and how he invests in other startups through his VC fund. His first business was a software company that helped banks identify fraud. He eventually signed over 400 banks as clients and sold the business - and he didn't even know what venture capital was when he started the business.

0:54 Becoming an Operator & Investor
4:31 Esteban's risk profile when investing
9:32 Going into a new industry (buying schools)
21:28 Economics of buying schools
33:02 Applying AI to roll-ups
43:21 AI for law firms - why it can't work


Connect with Sieva:

X: https://x.com/sievakozinsky
LinkedIn: https://www.linkedin.com/in/skozinsky
Newsletter: https://sievakozinsky.com

Connect with Esteban:

X: https://x.com/57cap
Website: https://www.zenda.vc/

Rafael Quinn is the co-founder of Alternative Holdings, a holding company with 9 portfolio companies in a variety of industries. In this interview, Rafael explains how he started a holdco by accident nearly 15 years ago. Rafael and his partner started by just buying one company, but soon found more attractive opportunities.

0:29 How he accidentally started a holding company
6:24 The first acquisition
9:25 Why not focus on one industry?
15:21 Structure of his HoldCo & how they get capital for deals
24:03 Investing criteria
33:30 Retaining the old owner
38:07 Restaurant companies
50:29 Plumbing companies

Connect with Sieva:

X: https://x.com/sievakozinsky
Newsletter: https://sievakozinsky.com

Connect with Rafael:

X: https://www.alternativeholdings.com/
Website: https://www.alternativeholdings.com/

Today I speak with Moses Kagan, a real estate investor and operator in Los Angeles. Moses goes over some specific real estate deals he's done, including how he got started with a rundown, half-renovated apartment building in east Los Angeles. Moses manages hundreds of millions in real estate and has the battle scars to prove it.

0:00 Introductions

0:55 His first deal

12:35 How to find tenants

16:40 Quitting his job

27:20 Math on new acquisitions

30:20 Seeding new real estate operator

35:30 How much should you pay for a deal?

44:30 Your own capital vs. other people's money

1:05:40 One of Moses' first deal

1:17:10 Immigrant stories

👉 Connect with Sieva

Website: www.sievakozinsky.com
X: https://x.com/SievaKozinsky
LinkedIn: www.linkedin.com/in/skozinsky/

👉 Connect with Moses

Website: https://kagansblog.com/
https://x.com/moseskagan

Connor Tomkies sold his business for a mid-8 figure payout to private equity. In this conversation, he explains how he sold SupportNinja, including how he hired an investment banker/broker, how he negotiated the fee for the banker, and how he made sure to get top dollar for his company.

Highlights:

0:38 Introduction
1:11 The process of selling the business
2:57 Fees
4:30 Public Comps
5:15 How do you position a business to sell?
6:10 Choosing a buyer