How hard is it actually to execute a roll up?

Wanted to gather some insight from people who have pursued or considered executing a roll-up strategy independently.

I do not think that I want to be a career PE investor, my primary interest in the space is to prepare me to take an entrepreneurial leap.

Am I vastly underestimating the difficulty of executing a roll up? My experience is in healthcare and I have always thought that after a few years in LMM PE that I would pick a healthcare niche to roll up and have a fat pay day. Is this even remotely realistic or is it just too competitive these days?

7 Comments
 

This is kind of a useless question. If I tell you it's extremely easy would that change how likely you are to pursue it? Or vice versa? Try it and see what happens.

A better question is what kind of difficulty is executing a roll-up. It's the operational kind. 

Sourcing, deal negotiation, financial analysis, building working trust, incentive alignment and post-close remediation and integration aren't conceptually difficult, they just require a blend of EQ, IQ and work ethic. And honestly you can be lacking in 1 of the 3 and still have a decent to successful roll-up. Enough work ethic can pretty much blast through any deficiencies in EQ or IQ imo although if I had to rank importance, EQ, work ethic and IQ in that order. In the LMM it's mostly about getting enough operators through the NDA funnel to even get to the point of closing 1 deal. 99% of business jobs are basically this at the end of the day - sales and some rote execution

 
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Most Helpful

Working on a business now, and a few buddies are running rollups. It's very difficult, but more because of interpersonal dynamics. The actual problems you're solving aren't that complicated, unless you're doing something deeply technical.

In IB/PE, you'll learn to push through long hours, manage your time, work quickly, be accurate, and communicate well with people. All these things will help you because they're good skills to have. But you're also going to run into problems that skill and polish won't help you fix. Like here are some actual issues either I or my entrepreneur friends had:

  • How do you learn about a "cliquey" industry from experts who don't trust outsiders when you have nothing to offer in return and will often be perceived as trying to sell something?
  • How do you convince someone with a cushy job and way more talent than you to join your team when you can't pay them yet?
  • How do you show a 55-year-old blue collar business owner that you're different from the 20 other finance bros calling them weekly to sell their business? 
  • How do you convince a minimum wage worker who is just there to collect their paycheck to do their job the right way?
  • How do you get an enterprise VP to take you seriously in a sales meeting if your only experience is in finance and you're competing against other enterprises?
  • How do you work daily with people who have a significantly different background than you (e.g. never finished high school but knows everything about making boilers) without alienating them or yourself?

The piece my friends brought up most often is working with people who don't have the same polish or level of motivation. It's definitely a huge change if you're used to being around hyper-motivated people from top backgrounds who always put work first. Wouldn't blame you for not wanting to leave that bubble, and I think back to it a lot too. But if you do a rollup, you have to be willing to go outside it.  

 

Works at Other

Working on a business now, and a few buddies are running rollups. It's very difficult, but more because of interpersonal dynamics. The actual problems you're solving aren't that complicated, unless you're doing something deeply technical.

In IB/PE, you'll learn to push through long hours, manage your time, work quickly, be accurate, and communicate well with people. All these things will help you because they're good skills to have. But you're also going to run into problems that skill and polish won't help you fix. Like here are some actual issues either I or my entrepreneur friends had:

  • How do you learn about a "cliquey" industry from experts who don't trust outsiders when you have nothing to offer in return and will often be perceived as trying to sell something?
  • How do you convince someone with a cushy job and way more talent than you to join your team when you can't pay them yet?
  • How do you show a 55-year-old blue collar business owner that you're different from the 20 other finance bros calling them weekly to sell their business? 
  • How do you convince a minimum wage worker who is just there to collect their paycheck to do their job the right way?
  • How do you get an enterprise VP to take you seriously in a sales meeting if your only experience is in finance and you're competing against other enterprises?
  • How do you work daily with people who have a significantly different background than you (e.g. never finished high school but knows everything about making boilers) without alienating them or yourself?

The piece my friends brought up most often is working with people who don't have the same polish or level of motivation. It's definitely a huge change if you're used to being around hyper-motivated people from top backgrounds who always put work first. Wouldn't blame you for not wanting to leave that bubble, and I think back to it a lot too. But if you do a rollup, you have to be willing to go outside it.  

Great comment.

I say this often on here, work on Main Street, learn how to relate to regular people.  When you’re in college, during periods of unemployment.  This type of work is not beneath you, it’s part of your education.  

Before opening my first business, I spent 6 months working a line position in that field, making $15 per hour (35 years old).  It was huge because I gained so much more credibility especially with customers (I’m not just a finance bro), and learned to relate to line staff and deal with everyday issues.  Also, created a vision of how I wanted to operate and the culture. 

My advice for people is to volunteer or get a part time job in the field you want to invest/operate, first.

Have compassion as well as ambition and you’ll go far in life. I am interested in digital immortality. Check out my blog at digitalimmortality.com
 

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