Why Private Equity CEOs Fail and How to Destroy Them All in 100 Days

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Here is the truth: most Private Equity CEOs fail within their first 18 months. It is not a test of intelligence; it is a test of speed to value and execution. The first 100 days are the make-or-break period where a new CEO proves their fitness, secures board alignment, and lays the foundation for exponential value creation. 

If you are stepping into a PE-backed CEO role, hesitation costs money—literally, as capital is always compounding. Your job is to survive your first three months and thrive.

In this essential CEO survival guide, Ryan Miller, breaks down the exact 100 Day Playbook used by top PE operating partners and successful portfolio company executives. 

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[THE HOST]: Ryan Miller is a recovering CFO turned angel investor in technology and energy.

Transcript

Ryan Miller  

My name is Ryan Miller, and for the past 15 years, I've helped hundreds of people to raise millions of dollars for their funds and for their startups. If you're serious about raising money, launching your business or taking your life to the next level, this show will give you the answers so that you too can enjoy your pursuit of Making Billions. Let's get into it. 

Ryan Miller  

You're going to be expected that your plan to the board is going to be sound, so that you win their hearts of gold, their minds of iron and their spines of steel, all to show that you have the same but you don't need to fly in there blind. 

Ryan Miller  

Here's the truth, most private equity CEOs fail within 18 months. It's not because they're not smart, it's because they don't deliver on the results in their first 100 days. See, private equity speed, it's survival, but today I'm going to give you more than advice. At the end of this video, I'm going to give you a full 100 day playbook with specific tasks, timelines and a plan that you can download and use. This is the roadmap that will help you survive your first 100 days and thrive in the role. In private equity, time is literally money. Capital is compounding at 20 to 25% a year, that means every month of delays burns or through returns. If a public company CEO looks at their calendar, then a private equity CEO is looking at their watch. So your first 100 days are where you prove you're the right leader. If you hesitate, you lose credibility with the board, but if you deliver, you gain the trust and freedom to lead. 

Ryan Miller 

So let's talk about taking stock of your job in the first month is not to act fast. It's to listen, assess and map out the terrain. Move too quickly here, and you'll make some bad calls, move too slowly and you'll look indecisive. So here's your checklist. Number one, board alignment, meet each member of the board, one on one, capture their expectations and their perspective on the deal thesis, the next one is investment thesis. Deconstruct it. Underwrite the model, understand everything you can. Know the value creation levers down, cold revenue growth, cost savings, working capital, M&A, all of it, know all of it. The next one is the organization and the talent that you have to work with. You want to assess your leadership team, rate the A, B and C, or however you want to do it, but just make sure that you have a good stock of who's who in the zoo as I like to say, you'll likely need to replace 30-40% of these level two leaders and 50-65% of your VPs. I mean, we'll see. It depends where you're coming in, but this is something that you may need to prepare for. The next one is figuring out your operating rhythm. So the best thing you can do is set up weekly executive reviews and establish finance dashboards, even if it's version one, just get started. Next one is the kickoff plan. So you want to draft your 100 day roadmap with visible early wins, so start knocking down, as we some people like to call the low hanging fruit. So the outcome by your 30th day is you want to achieve alignment with the board, clarity on the thesis and a team map with replacement decisions queued up ready to go. Now with the first 30 days in place, let's dive into taking action. 

Ryan Miller   

So now that the clock is ticking, this is where you really need to start making visible moves. The first step that you want to focus on is talent. Decide quickly who stays and who goes, if someone isn't cutting it, move fast. The next one is leadership hiring, fill those key gaps. CFO, COO, HR, rev ops, whoever it is, start filling those key leadership gaps. Then the next phase is strategy you want to finalize, say, 3-5 Strategic Priorities. 3-5 is that sweet spot that you're after. And remember, strategy is just a fancy word for approach, an efficient approach. So what are those are priorities that will help you achieve whatever approach you are that's going to go for your thesis. Then the next phase is you want to lock in early initiatives in your plan. Just launch quick wins like costs, cutting programs, pricing reviews or working capital cleanup. I remember when I was a CFO, that was one of the first things that I found when I went in, was working capital cleanup. We changed our cash conversion cycle, we did a lot of things that we got the working capital back on board and I did that within the first 100 days, and then we scaled it up after that. CEOs can do that, but set it and be visible about it. The next phase is a deep dive into the board. At about day 60, you want to hold your first major board review show progress and recalibrate. So the outcome by day 60 looks something like this. You got the right a team in place. You have strategic priorities locked in. You have visible wins on the board, and the board trusts you in your execution. 

Ryan Miller   

So finally, let's lock it in on you taking control of this starship. This is where you move from reading, to leading you want to set a 12 month strategy, translate those three to five priorities into a 12 month roadmap with budgets and headcount plans. The next thing you want to do is establish those dashboards to ensure that you're measuring so that you're managing, automate reporting, aim for monthly close in under five days. The next phase that you want to focus on as a newly minted CEO and captain of this starship is you want to look at inorganic growth. So you want to start scouting M&A screen for 10 advanced three and get at least one deal diligence ready. Then after that, you want to move on to governance, you want to lock in board cadence, decision rights and escalation pass. Company communication is the next phase on the next phase, you want to roll out your strategy at an all hands meeting, rally your team around you have and have clear, achievable goals. 

Ryan Miller 

Now finally, you want to lock it in so that by the end of your 100th day, you have a clear 12 month roadmap, reporting tools that are live, an M&A pipeline that's active and thriving and governance locked in, so that the company can feel your leadership and be energized. So by this point, you're going to be expected that your plan to the board is going to be sound, so that you win their hearts of gold, their minds of iron and their spines of steel, all to show that you have the same but you don't need to fly in there blind. I put all of this into a plan that you can download. It lays out every task, who owns it, the start and end of the week, success criteria, risk mitigations, all of it. It's the same kind of roadmap PE operating partners use to track new CEOs, and it's yours to use for your first 100 day plan. 

Ryan Miller 

So let's recap your 100 day playbook. Number one, build alignment with the board, then master the investment thesis. After that, make sure you assemble your A team fast, then deliver early wins, followed by locking in reporting and governance and finally, lead with conviction. If you do these six things, you won't just survive as a PE CEO. You will thrive. Now here's how to get the plan, SUBSCRIBE and leave a review, take a screenshot and DM it to me on Instagram at Making Billions Podcast. Once you send me that, I'll send you the link to download this personally and remember, this isn't theory, this is the exact roadmap that some of the best CEOs use. So save this, download the plan, and come back to it as you plan to execute, because in private equity, speed to value isn't optional, it's survival.

Ryan Miller 

Wow, what a show, I hope you enjoyed this episode as much as I did. Now, if you haven't done so already, be sure to leave a comment and review on new ideas and guests you want me to bring on for future episodes. Plus, why don't you head over to YouTube and see extra takes while you get to know our guests even better. And make sure to come back for our next episode, where we dive even deeper into the people, the process and the perspectives of both investors and founders. Until then, my friends, stay hungry, focus on your goals and keep grinding towards your dream of Making Billions.