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Apr 1, 2016 · 22m · top-founders

Quit $100k+ Private Equity to Move to South America, Does $1m Tax Business Now with Vincenzo Villamena of Online Tax Man EP 216

Vincenzo Villamena · 11m spoken Nathan Latka · 8m spoken
0:00 / 0:00

gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions

In this episode of The Top, host Nathan Latka interviews Vincenzo Villamena, who transitioned from corporate accounting and private equity to launch Online Tax Man, a remote international tax practice approaching one million dollars in annual revenue.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Nathan holds 43.4% of the talking time here. How this is scored →

Nathan as informed peer 3.3 Guest teaching 2.7 Guest disagreement 1.3 Nathan pushing back 3.3
05100:0010:0020:001:55–4:40 · Nathan as informed peer 2/10 Childhood Entrepreneurship: Selling Costco Candy Nathan probes into the early childhood economics of buying Costco candy and early career pay at PwC. The dynamic is conversational and humorous with playful host banter.4:40–7:30 · Nathan as informed peer 4/10 Entering Private Equity and the Reality of Compensation Nathan presses Vincenzo to explain the specifics of his private equity compensation package and clarify the concept of carried interest for the audience.7:30–10:38 · Nathan as informed peer 4/10 Private Equity Fundraising and Pitch Decks Nathan investigates the fund's fundraising pitch deck and questions what limited partners care most about when deciding whether to commit capital.10:39–13:45 · Nathan as informed peer 5/10 Roll-Up Investment Strategy and Deciding to Quit Vincenzo outlines the fund's medical billing roll-up strategy, and Nathan actively synthesizes and reframes the network effects and capital advantages of private equity roll-ups.13:46–17:23 · Nathan as informed peer 3/10 Moving to South America and Discovering the Expat Tax Niche Vincenzo educates the host on the complexities of expat tax compliance, while Nathan presses for concrete revenue metrics and seasonality breakdown.17:23–21:19 · Nathan as informed peer 2/10 How to Connect with Vincenzo Villamena During the Famous Five rapid-fire questions, Nathan aggressively teases the guest for pausing on the business book question, accusing him of searching online.1:55–4:40 · Guest teaching 1/10 Childhood Entrepreneurship: Selling Costco Candy Nathan probes into the early childhood economics of buying Costco candy and early career pay at PwC. The dynamic is conversational and humorous with playful host banter.4:40–7:30 · Guest teaching 3/10 Entering Private Equity and the Reality of Compensation Nathan presses Vincenzo to explain the specifics of his private equity compensation package and clarify the concept of carried interest for the audience.7:30–10:38 · Guest teaching 3/10 Private Equity Fundraising and Pitch Decks Nathan investigates the fund's fundraising pitch deck and questions what limited partners care most about when deciding whether to commit capital.10:39–13:45 · Guest teaching 4/10 Roll-Up Investment Strategy and Deciding to Quit Vincenzo outlines the fund's medical billing roll-up strategy, and Nathan actively synthesizes and reframes the network effects and capital advantages of private equity roll-ups.13:46–17:23 · Guest teaching 4/10 Moving to South America and Discovering the Expat Tax Niche Vincenzo educates the host on the complexities of expat tax compliance, while Nathan presses for concrete revenue metrics and seasonality breakdown.17:23–21:19 · Guest teaching 1/10 How to Connect with Vincenzo Villamena During the Famous Five rapid-fire questions, Nathan aggressively teases the guest for pausing on the business book question, accusing him of searching online.1:55–4:40 · Guest disagreement 1/10 Childhood Entrepreneurship: Selling Costco Candy Nathan probes into the early childhood economics of buying Costco candy and early career pay at PwC. The dynamic is conversational and humorous with playful host banter.4:40–7:30 · Guest disagreement 2/10 Entering Private Equity and the Reality of Compensation Nathan presses Vincenzo to explain the specifics of his private equity compensation package and clarify the concept of carried interest for the audience.7:30–10:38 · Guest disagreement 1/10 Private Equity Fundraising and Pitch Decks Nathan investigates the fund's fundraising pitch deck and questions what limited partners care most about when deciding whether to commit capital.10:39–13:45 · Guest disagreement 1/10 Roll-Up Investment Strategy and Deciding to Quit Vincenzo outlines the fund's medical billing roll-up strategy, and Nathan actively synthesizes and reframes the network effects and capital advantages of private equity roll-ups.13:46–17:23 · Guest disagreement 1/10 Moving to South America and Discovering the Expat Tax Niche Vincenzo educates the host on the complexities of expat tax compliance, while Nathan presses for concrete revenue metrics and seasonality breakdown.17:23–21:19 · Guest disagreement 2/10 How to Connect with Vincenzo Villamena During the Famous Five rapid-fire questions, Nathan aggressively teases the guest for pausing on the business book question, accusing him of searching online.1:55–4:40 · Nathan pushing back 2/10 Childhood Entrepreneurship: Selling Costco Candy Nathan probes into the early childhood economics of buying Costco candy and early career pay at PwC. The dynamic is conversational and humorous with playful host banter.4:40–7:30 · Nathan pushing back 4/10 Entering Private Equity and the Reality of Compensation Nathan presses Vincenzo to explain the specifics of his private equity compensation package and clarify the concept of carried interest for the audience.7:30–10:38 · Nathan pushing back 3/10 Private Equity Fundraising and Pitch Decks Nathan investigates the fund's fundraising pitch deck and questions what limited partners care most about when deciding whether to commit capital.10:39–13:45 · Nathan pushing back 3/10 Roll-Up Investment Strategy and Deciding to Quit Vincenzo outlines the fund's medical billing roll-up strategy, and Nathan actively synthesizes and reframes the network effects and capital advantages of private equity roll-ups.13:46–17:23 · Nathan pushing back 4/10 Moving to South America and Discovering the Expat Tax Niche Vincenzo educates the host on the complexities of expat tax compliance, while Nathan presses for concrete revenue metrics and seasonality breakdown.17:23–21:19 · Nathan pushing back 4/10 How to Connect with Vincenzo Villamena During the Famous Five rapid-fire questions, Nathan aggressively teases the guest for pausing on the business book question, accusing him of searching online.

speaking balance: gold is Nathan, purple is the guest (3 minute bins)

0:00 · Nathan 78% · guest 22%0:00 · Nathan 78% · guest 22%3:00 · Nathan 30.4% · guest 69.6%3:00 · Nathan 30.4% · guest 69.6%6:00 · Nathan 23.9% · guest 76.1%6:00 · Nathan 23.9% · guest 76.1%9:00 · Nathan 30.4% · guest 69.6%9:00 · Nathan 30.4% · guest 69.6%12:00 · Nathan 14.9% · guest 85.1%12:00 · Nathan 14.9% · guest 85.1%15:00 · Nathan 25.4% · guest 74.6%15:00 · Nathan 25.4% · guest 74.6%18:00 · Nathan 75.7% · guest 24.3%18:00 · Nathan 75.7% · guest 24.3%21:00 · Nathan 88.9% · guest 11.1%21:00 · Nathan 88.9% · guest 11.1%
Sharpest disagreement ▶ 19:53 Defending against fake book search accusation

Vincenzo defends himself after Nathan accuses him of stalling and googling a book title on the spot.

 Hardest push from Nathan ▶ 19:47 Calling out suspected book search

Nathan interrupts Vincenzo's hesitation to challenge whether he is looking up a book online rather than giving an authentic answer.

 Biggest teaching moment ▶ 14:45 Expat tax rules and market opportunity

Vincenzo details the specific complexities US expats face, including foreign bank reporting and the Foreign Earned Income Exclusion.

 Nathan holds their own ▶ 12:56 Synthesizing PE roll-up strategy

Nathan demonstrates solid financial knowledge by articulating how roll-ups leverage concentrated capital and network advantages to create value beyond passive investing.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Childhood Entrepreneurship: Selling Costco Candy 2112 Nathan probes into the early childhood economics of buying Costco candy and early career pay at PwC. The dynamic is conversational and humorous with playful host banter.
Entering Private Equity and the Reality of Compensation 4324 Nathan presses Vincenzo to explain the specifics of his private equity compensation package and clarify the concept of carried interest for the audience.
Private Equity Fundraising and Pitch Decks 4313 Nathan investigates the fund's fundraising pitch deck and questions what limited partners care most about when deciding whether to commit capital.
Roll-Up Investment Strategy and Deciding to Quit 5413 Vincenzo outlines the fund's medical billing roll-up strategy, and Nathan actively synthesizes and reframes the network effects and capital advantages of private equity roll-ups.
Moving to South America and Discovering the Expat Tax Niche 3414 Vincenzo educates the host on the complexities of expat tax compliance, while Nathan presses for concrete revenue metrics and seasonality breakdown.
How to Connect with Vincenzo Villamena 2124 During the Famous Five rapid-fire questions, Nathan aggressively teases the guest for pausing on the business book question, accusing him of searching online.

Statements from this episode (8)

Disclosure
Villamena: Starting Salary at PwC Was Around $55,000
“Starting out, it was around 55.”
Vincenzo Villamena Apr 1, 2016 ▶ 3:24
Opinion
Villamena: Big Four Accounting Firms Are Like Post-College Frat Parties
“The thing about PwC is it, I mean, and really the big four in general is like, you know, if you want to be an accountant, it's a great place to start off. I mean, you know, every, it's really young organization. It's kind of like a frat party. Everyone from co…”
Vincenzo Villamena Apr 1, 2016 ▶ 3:34
Assertion Contradicted
Villamena: 80% to 90% of Big Four Hires Leave After CPA Licensure
“Pretty much, you know, 80, 90% of the people that, that, that start working in big four accounting just end up, you know, getting their, fulfilling their CPA licensure requirements and then getting, getting out of Dodge.”
Vincenzo Villamena Apr 1, 2016 ▶ 4:19
Disclosure
Villamena: Private Equity Firm Promised Carried Interest But Never Delivered
“I mean, you know, we were promised carry, which we never got.”
Vincenzo Villamena Apr 1, 2016 ▶ 5:32
Assertion Not publicly verifiable
Villamena: Pegasus Blue Star Fund closed only around $100M
“We never ended up doing the second rounds. I mean, we didn't get the full fund. We maybe closed like a hundred or something.”
Vincenzo Villamena Apr 1, 2016 ▶ 7:52
Assertion Not checkable as stated
Villamena: Pegasus Blue Star Fund Achieved Over 20% Healthcare IRR
“So, the IRR, I mean, it was definitely like above 20%.”
Vincenzo Villamena Apr 1, 2016 ▶ 10:49
Assertion Not checkable as stated
Villamena: Online Tax Man generated around $20K-$30K in January 2016
“Probably 20, 30,000, something like that, maybe more.”
Vincenzo Villamena Apr 1, 2016 ▶ 16:25
Prediction Not checkable as stated
Villamena: Online Tax Man will generate just short of $1M in 2016
“Yeah, I mean, 20, 2016, we're talking about probably just short of a million.”
Vincenzo Villamena Apr 1, 2016 ▶ 16:45
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