Ankur Nagpal sold his business, Teachable, for $250 million. Now, he's focused on making people aware of tax optimization strategies (inspired by what he wish he know when starting his business).

I asked Ankur how he knew when to sell his business, how the process went, and for some tips on lowering tax bills when selling a business.

0:00 Intro
0:57 How Ankur sold Teachable
9:57 Structure of the Deal
11:40 Why he raised VC money 
14:45 How he went from retired to running his next business
20:29 Carry's business model
23:05 Tax loopholes
26:40 How Ankur markets his new business
33:32 Monetization
38:40 The VC business model
41:30 QSBS



👉 Connect with Sieva

Website: www.sievakozinsky.com
X: twitter.com/SievaKozinsky
LinkedIn: www.linkedin.com/in/skozinsky/
Substack: www.thebusinessacademy.substack.com/

David Rodnitzky sold his agency for $65 million - and then bought it back for $5 million. And then he sold it again for way more than $65 million. 

Listen to this fascinating conversation about how to scale a marketing agency, how much you can sell your agency for, and what his margins are. 

0:00 Intro
3:20 How David sold and re-bought his agency
11:05 How much can you sell an agency for?
13:50 Fire yourself from jobs before you sell
18:03 Raising his prices from $5k to $25k per month
22:10 What kind of agencies would you buy?
29:56 Pitching Apple (and why they didn't hire him)
32:40 Getting a $70k/month client
33:45 Multiple for agencies


👉 Connect with Sieva

Website: www.sievakozinsky.com
X: twitter.com/SievaKozinsky
LinkedIn: www.linkedin.com/in/skozinsky/
Substack: www.thebusinessacademy.substack.com/

Jameson Haslam left his banking & private equity career to start a boring, home deck business in San Diego. He's already grown it to $1.5 million in annual revenue in a couple years. We talk about why he chose a boring business, how he sold his first project before he even had a business, and how he plans to scale it up.

0:00 Introduction
3:15 Airbnb Arbitrage
5:55 Picking the home deck niche
13:45 Generating leads
20:29 This year's revenue & profit
23:10 The growth playbook
27:10 Collecting cash from customers
31:45 The team & overseas hiring
36:40 How Jameson uses Instagram


👉 Connect with Sieva

Website: www.sievakozinsky.com
X: twitter.com/SievaKozinsky
LinkedIn: www.linkedin.com/in/skozinsky/
Substack: www.thebusinessacademy.substack.com/ 


👉 Connect with Jameson

X: https://x.com/jamesonhaslam
Instagram: https://www.instagram.com/west.coast.deck/
Website: https://www.westcoastdeck.com/

Please leave a review if you enjoyed this episode!

In today’s episode Boring Businesses, I’m joined by Josh York, founder and CEO of GymGuyz, the largest in-home and on-site personal training company in the world.

Josh’s entrepreneurial journey is a testament to relentless grit, vision, and an unwavering commitment to innovation. He offers insights into leadership, scaling a franchise, and maintaining a strong company culture, all while motivating others to push past limits—both in fitness and life.

Timestamps:

00:00 Trailer
00:31 Creating a culture with fuel and drive
04:21 Sending a tire to Nike founder Phil Knight
08:31 Building resilience
10.41 Getting obsessed with competition
17:24 Negative experiences fuel career change
19:53 Creating career paths for personal trainers to succeed
27:35 Scaling a fitness franchise
32:49 Core requirements of success
37:15 Learning from our mistakes
40:26 Owning multiple locations
46:16 Company culture, being present, and balance
54:25 Leading by example

👉 Connect with Sieva

Website: www.sievakozinsky.com
X: twitter.com/SievaKozinsky
LinkedIn: www.linkedin.com/in/skozinsky/
Substack: www.thebusinessacademy.substack.com/ 


👉 Connect with Josh

X: https://x.com/joshyorkgg
Instagram: www.instagram.com/joshyorkgg/ 
LinkedIn: www.linkedin.com/in/joshyorkgymguyz/


If you enjoyed the episode, please leave a review to support the show. 🙏

When buying a business, should you keep the old owner on or hire your own operator?

The short answer is we've done both. In this video, I go into some examples and the nuances of when keeping the old owner on won't work. Let me know if you have other questions for me to answer.

If you like content about buying companies, investing, and building holding companies, subscribe to my weekly newsletter: https://sievakozinsky.com


👉 Connect with Sieva

X:   / sievakozinsky  
LinkedIn:   / skozinsky

Today I'm answering questions from the audience. "How do I sell my business for the most money possible?" is one of the most common questions I get. Since I've bought 20+ companies at Enduring Ventures, I have a long list of criteria I look for when buying a business.

👉 Connect with Sieva

Website: https://www.sievakozinsky.com/
X:   / sievakozinsky  
LinkedIn:   / skozinsky

I spoke with Aaron Harper, who's turning a boring business into a national franchise. He found Rolling Suds, a pressure washing business that does $2 million in annual revenue with 37% margins, and has sold 200+ franchise territories in less than 2 years. And he's done this twice before, with a drywall patching company and a carpet cleaning business.

Highlights:

0:00 Introductions
0:35 Aaron's background
11:30 Turning around a franchise business
14:40 Generating leads for franchises
23:02 Economics of a franchising business
27:30 Rolling Suds' moat
41:30 How to operate a Rolling Suds franchise
54:40 Structure of his deal with Rolling Suds


👉 Connect with Sieva

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

👉 Connect with Aaron

X: https://x.com/AaronHarperCEO


If you enjoyed the episode, please leave a review on Apple Podcasts and Spotify to support the show. 🙏


#entrepreneur #business #personaldevelopment

I spoke with Johnny Robinson, an expert on the home cleaning business model. One of the biggest takeaways was how Johnny bought a $250k/year business for just $1k down with a creative deal structure that others can replicate. He also talked me through the economics of a home cleaning business, how his course business works, and another creative acquisition he did.

Highlights:

00:00 Introductions
1:44 How Johnny started his first cleaning business
6:40 Building referral partnerships
14:05 Helping mom make $150k/year
17:50 Networking groups
18:55 Buying a $250k business for $1k down
21:55 Buying a solar panel business
25:05 Starting a home cleaning business
30:25 How to make money on ads
33:30 How to hire reliable cleaners
35:50 Johnny's course business
44:25 How big can a cleaning business be?


👉 Connect with Sieva

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

👉 Connect with Johnny

X: https://x.com/squeegeegod
Website: https://www.homeserviceacademy.co/


If you enjoyed the episode, please leave a review on Apple Podcasts and Spotify to support the show. 🙏


#entrepreneur #business #personaldevelopment

I talked with Dr. Peter Boulden, the owner of 8 dental practices in Atlanta. He taught me his strategies for shifting from a solo practitioner dentist to the developer and owner of 8 dental practices (and still growing).

Highlights:

0:00 Introductions
7:40 The McDonald's Model
15:50 Dental Roll-ups: Good or Bad Idea?
17:45 Economics of Dental Practices
23:20 Recruiting A+ Dentists
30:25 SOPs for his dental practices
49:10 How to Sell Dental Services
58:05 Managing Partnerships
1:06:50 Peter's Vision & Goals


👉 Connect with Sieva

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

👉 Connect with Peter

X: https://x.com/peterboulden
Website: https://www.bulletproofdentalpractice.com/


If you enjoyed the episode, please leave a review on Apple Podcasts and Spotify to support the show. 🙏


#entrepreneur #business #personaldevelopment

I talked with Eric Pacifici, founder of SMB Law Group LLP. His team has closed $950 million in SMB acquisitions last year alone, after founding the firm only a couple years ago. Eric grew his firm with a combination of his connections from working in big law, and his insightful Twitter account (100k+ followers). 

Highlights:

00:00 Introductions
03:40 Eric's Twitter Account
06:33 SMB Law Group's Growth
10:00 How much should you pay your attorney?
23:05 How to Negotiate terms in your deal
27:10 Most common reasons builds blow up
33:20 Stock vs. Asset sales

👉 Connect with Sieva

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

👉 Connect with Eric

X: https://x.com/SMB_Attorney
Law Firm: https://www.smblaw.group/


If you enjoyed the episode, please leave a review!


#entrepreneur #business #personaldevelopment