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๐Ÿ‘ค Speaker
9500 total appearances

Appearances Over Time

Podcast Appearances

Invest Like the Best with Patrick O'Shaughnessy
Royce Yudkoff & Rick Ruback - Entrepreneurship Through Acquisition - [Invest Like the Best, EP.423]

And we know the stats about how big that generation was and how many of these companies exist. If you compare the next 10 years to the prior 10, do you think the supply side of the story is better? There will be more of them that are more fit to be bought. What trends do you see, if at all, in the base of companies and what the motivations of the sellers are?

Invest Like the Best with Patrick O'Shaughnessy
Royce Yudkoff & Rick Ruback - Entrepreneurship Through Acquisition - [Invest Like the Best, EP.423]

And we know the stats about how big that generation was and how many of these companies exist. If you compare the next 10 years to the prior 10, do you think the supply side of the story is better? There will be more of them that are more fit to be bought. What trends do you see, if at all, in the base of companies and what the motivations of the sellers are?

Invest Like the Best with Patrick O'Shaughnessy
Royce Yudkoff & Rick Ruback - Entrepreneurship Through Acquisition - [Invest Like the Best, EP.423]

But there's a lot of businesses out there that need to transition. I have lots of questions that are under the umbrella category of technology. The first is related to the types of businesses that you do and don't see people buy. And we have such a big sample now, like I'm sure there's some central tendencies.

Invest Like the Best with Patrick O'Shaughnessy
Royce Yudkoff & Rick Ruback - Entrepreneurship Through Acquisition - [Invest Like the Best, EP.423]

But there's a lot of businesses out there that need to transition. I have lots of questions that are under the umbrella category of technology. The first is related to the types of businesses that you do and don't see people buy. And we have such a big sample now, like I'm sure there's some central tendencies.

Invest Like the Best with Patrick O'Shaughnessy
Royce Yudkoff & Rick Ruback - Entrepreneurship Through Acquisition - [Invest Like the Best, EP.423]

You always hear roofing or HVAC or like stuff related to the home or basic things that in 10 years are still going to be roofs and probably an AI won't install them. If it does, you know, all bets are off. Do you ever see people buying more traditionally software or technology-driven businesses as searchers at all?

Invest Like the Best with Patrick O'Shaughnessy
Royce Yudkoff & Rick Ruback - Entrepreneurship Through Acquisition - [Invest Like the Best, EP.423]

You always hear roofing or HVAC or like stuff related to the home or basic things that in 10 years are still going to be roofs and probably an AI won't install them. If it does, you know, all bets are off. Do you ever see people buying more traditionally software or technology-driven businesses as searchers at all?

Invest Like the Best with Patrick O'Shaughnessy
Royce Yudkoff & Rick Ruback - Entrepreneurship Through Acquisition - [Invest Like the Best, EP.423]

And maybe just say a word about the central pockets or tendencies of the kinds of businesses that meet the three criteria or four criteria that you laid out earlier and what doesn't, despite being important businesses.

Invest Like the Best with Patrick O'Shaughnessy
Royce Yudkoff & Rick Ruback - Entrepreneurship Through Acquisition - [Invest Like the Best, EP.423]

And maybe just say a word about the central pockets or tendencies of the kinds of businesses that meet the three criteria or four criteria that you laid out earlier and what doesn't, despite being important businesses.

Invest Like the Best with Patrick O'Shaughnessy
Royce Yudkoff & Rick Ruback - Entrepreneurship Through Acquisition - [Invest Like the Best, EP.423]

One of the things that we've been studying recently is Asurion, thanks to a project with Will Thorndyke covering that company. And it makes me wonder how often you've seen that, what I'll call extreme outlier venture type multiple of capital outcome from this space versus the more like lower variance, whatever the 33% a year for 10 years math is for MOIC.

Invest Like the Best with Patrick O'Shaughnessy
Royce Yudkoff & Rick Ruback - Entrepreneurship Through Acquisition - [Invest Like the Best, EP.423]

One of the things that we've been studying recently is Asurion, thanks to a project with Will Thorndyke covering that company. And it makes me wonder how often you've seen that, what I'll call extreme outlier venture type multiple of capital outcome from this space versus the more like lower variance, whatever the 33% a year for 10 years math is for MOIC.

Invest Like the Best with Patrick O'Shaughnessy
Royce Yudkoff & Rick Ruback - Entrepreneurship Through Acquisition - [Invest Like the Best, EP.423]

How often are you seeing true outliers emerge from this style of investing in that bizarre category of Asurion, which you could put up against any venture investment of all time?

Invest Like the Best with Patrick O'Shaughnessy
Royce Yudkoff & Rick Ruback - Entrepreneurship Through Acquisition - [Invest Like the Best, EP.423]

How often are you seeing true outliers emerge from this style of investing in that bizarre category of Asurion, which you could put up against any venture investment of all time?

Invest Like the Best with Patrick O'Shaughnessy
Royce Yudkoff & Rick Ruback - Entrepreneurship Through Acquisition - [Invest Like the Best, EP.423]

One of my favorite lines of yours, Royce, I think it was you that said this to me, which is that the lower middle market is the only industry in the world where your best competition leaves every year. Yes, that's right. I did say that. Can you talk a little bit about that observation and dynamic?

Invest Like the Best with Patrick O'Shaughnessy
Royce Yudkoff & Rick Ruback - Entrepreneurship Through Acquisition - [Invest Like the Best, EP.423]

One of my favorite lines of yours, Royce, I think it was you that said this to me, which is that the lower middle market is the only industry in the world where your best competition leaves every year. Yes, that's right. I did say that. Can you talk a little bit about that observation and dynamic?

Invest Like the Best with Patrick O'Shaughnessy
Royce Yudkoff & Rick Ruback - Entrepreneurship Through Acquisition - [Invest Like the Best, EP.423]

Yeah, it's a fascinating dynamic at play, which I guess makes it sort of an evergreen opportunity set. Back to thinking about the companies, I'm curious what the things are that are the most common, subtle red flags that through pattern recognition

Invest Like the Best with Patrick O'Shaughnessy
Royce Yudkoff & Rick Ruback - Entrepreneurship Through Acquisition - [Invest Like the Best, EP.423]

Yeah, it's a fascinating dynamic at play, which I guess makes it sort of an evergreen opportunity set. Back to thinking about the companies, I'm curious what the things are that are the most common, subtle red flags that through pattern recognition

Invest Like the Best with Patrick O'Shaughnessy
Royce Yudkoff & Rick Ruback - Entrepreneurship Through Acquisition - [Invest Like the Best, EP.423]

And just seeing a million of these reps through your students and directly yourselves, you've built up over time of not the obvious, like terrible customer concentration or completely non-recurring, you know, the opposite of the things that you've said, but more just the little ones like, oh, watch out for this thing or this thing. Maybe we'll call them yellow flags, not red flags.

Invest Like the Best with Patrick O'Shaughnessy
Royce Yudkoff & Rick Ruback - Entrepreneurship Through Acquisition - [Invest Like the Best, EP.423]

And just seeing a million of these reps through your students and directly yourselves, you've built up over time of not the obvious, like terrible customer concentration or completely non-recurring, you know, the opposite of the things that you've said, but more just the little ones like, oh, watch out for this thing or this thing. Maybe we'll call them yellow flags, not red flags.

Invest Like the Best with Patrick O'Shaughnessy
Royce Yudkoff & Rick Ruback - Entrepreneurship Through Acquisition - [Invest Like the Best, EP.423]

What are some of the most interesting things in that category?

Invest Like the Best with Patrick O'Shaughnessy
Royce Yudkoff & Rick Ruback - Entrepreneurship Through Acquisition - [Invest Like the Best, EP.423]

What are some of the most interesting things in that category?