If you're a PE investor or executive, you know the job: to make the investment thesis happen. Sounds straightforward. But it’s hard (especially nowadays). 

And usually, it's not the deal structure or market forces that get you. It's the people stuff:

• Leaders who aren’t moving at the pace of PE
• Talent gaps you acted on 18 months too late
• Strategy decks that never translate to execution
• Boards and management firing past each other

If you know, you know. 

I'm Dan. I've spent nearly two decades in PE—as an investor at a top-decile firm, as a portfolio company CEO/operator, and as an advisor to dozens of PE-backed companies. I’ve played across the positions. 

These days, I help PE-backed companies get 3 things right: 

→ Value Creation READINESS – Pre-close org and leadership diligence. Does a target actually have the leadership, talent, and culture to deliver your thesis?

→ Value Creation PLANNING – Getting the board and ELT aligned on the value creation plan, usually within the first 100 days post-acquisition.

→ Value Creation LEADERSHIP – Executive assessment and leadership development to ensure you have leaders who can deliver. 

Beyond advisory work: 

→  Wrote Winning Moves, the bestselling playbook on PE value creation
→  Co-founded Ascend, a leadership accelerator for execs in PE-backed companies
→  Teach a first-of-its-kind course on value creation at Chicago Booth
→  Guest lectured at Kellogg, Haas, MIT, HBS, and GSB
→  Now living that sweet suburban dad life in Cincy after years in SF and Chicago

Want to see how I think about this stuff?

•  Grab a copy of Winning Moves @ Amazon
•  Learn about our PE executive accelerator @ ascendforleaders.com 
•  Follow me for perspectives on value creation, leadership, and pizza

Dan Cremons

15 landmines that blow up first-time PE-backed CEOs. 

I've worked with dozens of first-time CEOs.
Been one myself.
Stepped on most of these landmines.

• Trying to be everyone's friend
• Being blind to your blind spots
• Overrelying on authority to lead
• Pretending you have it all figured out
• Not picking up on subtle board clues
• Getting stuck within the "CEO bubble"
• Failing to ally with and use your board
• Sitting on important decisions too long
• Focusing too heavily on the short-term 
• Forgetting your people are watching you
• Failing to focus on what's most important
• Rushing critical hires / slow-pedaling fires
• Failing to get your leadership team aligned
• Ignoring the political dynamics around you
• Giving underperformers too many chances

What else?

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Ascend

Winning Moves

Ascend - New

Operator's Edge

Grab a copy here → https://www.ascendforleaders.com/the-operators-edge-sign-up

Former PE Investor & CEO  //  Current PE Advisor  //  Author  //  𝘏𝘦𝘭𝘱𝘪𝘯𝘨 𝘢𝘮𝘣𝘪𝘵𝘪𝘰𝘶𝘴 𝘗𝘌-𝘣𝘢𝘤𝘬𝘦𝘥 𝘤𝘰𝘮𝘱𝘢𝘯𝘪𝘦𝘴 𝘢𝘤𝘤𝘦𝘭𝘦𝘳𝘢𝘵𝘦 𝘷𝘢𝘭𝘶𝘦 𝘤𝘳𝘦𝘢𝘵𝘪𝘰𝘯

Fellow PE professionals and execs: 

Wondering whether a target acquisition has the leadership and talent to make your investment thesis a reality? 

Not sure whether you have the right leaders in critical portfolio company roles?

Tired of losing time and momentum when a recently acquired company gets off to a slow start post-acquisition?

I get it. I’ve been in your shoes as a PE investor and CEO/CXO myself. 13+ amazing years with an innovative & top-performing MM PE firm.

Early on in my PE career, I learned the hard way that neglecting to (1) perform org due diligence, (2) get the right team onto the field quickly post-closing, (3) align on a clear value creation plan had costly consequences.  

🚫 Losing precious time
🚫 Putting growth & value creation at risk
🚫 Leaving returns on the table

But over years of learning from the best and lots of trial-and-error as a PE ops professional & executive, I figured out a thing or two about: 

→ How to size up a target’s leadership & value creation readiness BEFORE investing.
→ How to ensure you have the right leaders in the most critical port-co roles
→ How to get newly-acquired companies off to a strong start in the First 100. 

In 2021, I spun out of an in-house PE role so I could help more PE firms and their portfolio companies 𝗮𝗰𝗰𝗲𝗹𝗲𝗿𝗮𝘁𝗲 𝘃𝗮𝗹𝘂𝗲 𝗰𝗿𝗲𝗮𝘁𝗶𝗼𝗻 in 3 specific ways:

• Assessing value creation readiness pre-acquisition → 𝙨𝙤𝙡𝙪𝙩𝙞𝙤𝙣: 𝙤𝙧𝙜𝙖𝙣𝙞𝙯𝙖𝙩𝙞𝙤𝙣𝙖𝙡 𝙙𝙪𝙚 𝙙𝙞𝙡𝙞𝙜𝙚𝙣𝙘𝙚 - https://bit.ly/47HzPol

• Getting the right team onto the field post-acquisition → 𝙨𝙤𝙡𝙪𝙩𝙞𝙤𝙣𝙨: 𝙩𝙖𝙡𝙚𝙣𝙩 𝙖𝙨𝙨𝙚𝙨𝙨𝙢𝙚𝙣𝙩 // 𝙝𝙞𝙧𝙞𝙣𝙜 𝙩𝙧𝙖𝙞𝙣𝙞𝙣𝙜 - https://bit.ly/3T9yO3Z

• Getting off to a fast and focused start in the critical First 100 days → 𝙨𝙤𝙡𝙪𝙩𝙞𝙤𝙣: 𝙁𝟭𝟬𝟬 𝙫𝙖𝙡𝙪𝙚 𝙘𝙧𝙚𝙖𝙩𝙞𝙤𝙣 𝙥𝙡𝙖𝙣𝙣𝙞𝙣𝙜 - https://bit.ly/3GtWj02

* * * * * 

Want to learn more about how to do these things, but don’t want to work with me yet? No prob. You can check out: 

→ My bestselling book on PE value creation >>  www.winningmoves.co

→ This free workshop on how to approach organizational due diligence >> https://bit.ly/3rCfWiL

→ This free workshop on leadership assessment >> https://bit.ly/3RJOIRU 

→ This free workshop on how to win the First 100 >> http://bit.ly/3rCjPEy 

→ Learnings, practical advice, and the occasional dog photo I post daily  >>  [hit “Follow”]

Former PE Investor & CEO // Current PE Advisor // Author // 𝘏𝘦𝘭𝘱𝘪𝘯𝘨 𝘢𝘮𝘣𝘪𝘵𝘪𝘰𝘶𝘴 𝘗𝘌-𝘣𝘢𝘤𝘬𝘦𝘥 𝘤𝘰𝘮𝘱𝘢𝘯𝘪𝘦𝘴 𝘢𝘤𝘤𝘦𝘭𝘦𝘳𝘢𝘵𝘦 𝘷𝘢𝘭𝘶𝘦 𝘤𝘳𝘦𝘢𝘵𝘪𝘰𝘯

A value creation plan doesn’t have to be a 50-line, color-coded Gantt chart masterpiece.

Complexity feels safe and looks impressive. But it’s often a trap.

Keep it straightforward: 

1️⃣ Value Drivers: Retention? Expansion? New logos? Pricing? 

2️⃣ Objective: Be specific. “Increase X from Y to Z by [date].”

3️⃣ Winning Moves: Tactical, actionable initiatives to make it happen.

4️⃣ Indicators: The metrics you’ll monitor to know it’s on-track.

5️⃣ Owner: Who is the owner? Right person.

The simpler it is, the greater the likelihood it'll get executed. 

* * * * * 

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A search funder pitched me on his early childhood education thesis a few months back. Sharp guy, and had the whole thesis locked in:

→ Attractive unit economics
→ Strong operating leverage
→ Recession-resistant demand
→ Fragmented market ripe for consolidation

He envisioned himself taking an "active role." 

This was beautiful on paper. But halfway through, I asked if he had kids. He doesn't.

I have two of them, both in childcare. Which gave me a few notes on his thesis:

• Brutal staff turnover
• Dealing with nutty parents
• State regulators who show up unannounced
• That kid who always bites everyone (read: mine)
• The HVAC that breaks in August. Always August.
• The parents who are 30 minutes late at pickup. Again.
• The hallway that smells like diapers by end of day. Everday. 
• Norovirus ripping through the toddler room (and then the staff)
• One resignation away from calling in favors from family members
• Teachers making $18/hour for one of the tougher jobs imaginable
• The impossible math of mandated ratios when someone calls in sick

Classic case of: the thesis is clean... but the reality is messsssy. 

This isn't a knock on the searcher. He'll figure it out. But some businesses look way better/easier in Excel than they feel in real life.

Enormous respect for the people who run these places. Not for the faint of heart.

Just kicked off our latest Ascend cohort in snowy Colorado. 20 PE-backed executives across different industries and roles.

What struck me most: how fast the trust & bonds formed.

Within hours, they were challenging each other, supporting each other, and having the kind of honest conversations that are hard to find elsewhere.

That's one of the things I love about this program. Leaders in PE-backed companies often feel isolated. 

But put them in a room with other growth-minded peers... and the walls come down fast.

A few themes we kept hearing: 

→ "This was deeper than I expected."
→ "We're way more similar than different."
→ "I have much more clarity and confidence."

So grateful I get to do this work, and support + learn from leaders like these.

Christopher Adam Kenny Jordan Lora Paul James Timothy Josh Ryan Dan Adam Kelly Holly Chris Michael Sanjay Grift 

(More info on Ascend in the comments)

A PE-backed CEO's job is hard. But when you boil it down, it's also not complicated. 5 things the CEO must own and nail ↓

PE Backed CEO Job Description in 5 Points

Just wrapped the 6-month journey with our latest Ascend cohort of PE execs. And I'm reminded why I do this work: 

→ Lightbulb moments
→ Moments of real authentic connection
→ Leaders challenging each other to grow
→ A space where execs can actually be real
→ Swapping lessons / playbooks across industries

Six months ago, 16 strangers on a Zoom call. 
Now, a community invested in each other's success.

That kind of connection is rare in PE.
Feeling so lucky I get to help create it.

Excited to launch our next cohort this week!

(More info on the program in the comments. Enrolling now for our 2H26 groups.)

Boomer Brian Tim Ryan Galen Joe Derek Matt Lou Steven Ricardo Seth Ryan Felipe Grift

Chief Executive Officer at Red White & Blue Thrift

General Manager, Acme Finishing, LLC Powder Coating - Liquid Coating - Architectural Coating - Serving Major OEMs and their suppliers

Espire Dental, Chief Executive Officer

Chief Strategy Officer

VP, Finance & Accounting at Portnox

Portfolio Operations & GTM Value Creation Leader

GM at Pyramid Roofing | Vertex Service Partners

Purveyor of Pipe Nipples + Fittings

Tax Partner, Insero Advisors, LLC

Chief Operating Officer

4 x SVP Private Equity value creator | Driving digital transformation, revenue generation, and customer success with operational excellence | Professional Services, Managed Services, SaaS, Cloud, AI, CRM, ERP

Chief Executive Officer @ MojoTech

Chief Revenue Officer @ Meal Ticket

CTO, Full-stack Developer and UX Designer.

CEO of Thoughtium | Co-Founder of Ascend Leadership Accelerator

It's easy for PE firms to put "people matter" or "people first" on their websites. 
It's MUCH harder to build the systems that actually: 

• Attract talent 
• Assess talent 
• Lead talent 
• Retain talent 
• Develop talent 
• Unlock talent 

We're in the talent era of private equity now. People drive performance. 

So stop professing your edge. 
And start actually building it.

LAUNCH ALERT: just released Volume 1 of The Operator's Edge! It's a semi-annual briefing for PE operators and those who support them (operating partners, talent, portfolio ops, etc). 

Inside: 10 practical articles on the stuff that actually matters when you're running a PE-backed company.

One beta reader said, "I would pay for this." We decided to keep it free anyway.

Grab a copy at the link below 👊

Ineffective PE board meetings waste time, intelligence, and $$. Good ones create real leverage. Here are 5 common board meeting failure modes and how to spot them ↓

1. The Congressional Hearing
↳ Management vs. Board. Adversarial energy.
↳ Board asks "gotcha" questions to look smart
↳ Result: Zero collaboration, all performance theater

2. The Show-and-Tell
↳ 3 hours of updates no one needed
↳ Little time spent on actual problems / opps
↳ Result: Everyone leaves exhausted and nothing changes

3. The Free-for-All
↳ No agenda, facilitation. No focus.
↳ 45 minutes debating something that doesn't move the needle
↳ Result: Meeting wanders and critical issues never get discussed

4. The Loose End
↳ Great discussion, zero decisions
↳ No one recaps what was agreed to
↳ Result: Same conversation happens next quarter

5. The Leaf in the Wind
↳ No shared vision. No clear strategy.
↳ Discussions aren't tethered to a clear direction
↳ Result: The meeting drifts (and so does the business)

If your board meetings resemble any of these, no time like the beginning of the new year to get them tuned up. 

* * * * * 
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If you believe talent is important to PE returns, tell me: how much of your time in board meetings is spent discussing talent?

Pro Tip: Make talent talk a standing, recurring topic in board meetings.

Every. 
Single. 
Meeting.

Just in time for Q1 board meeting season... here's how ↓

How to Talk Talent in PE Board Meetings

Cultural transformation in PE port-co's almost always requires leadership transformation. Culture won't change if leaders don't change.

For cultural change to take hold, it is on leaders to: 

① ADVOCATE – It's what you say
→ Communicate the cultural changes clearly
→ Explain the "why" and the "what's in it for them"
→ Your team needs to hear it, understand it, and believe it

② MODEL – It's what you do
→ Walk the talk
→ Demonstrate the behaviors and mindsets you want to see
→ Your actions set the standard (not some slide deck)

③ OPERATIONALIZE – It's what you implement
→ Systematize the change
→ Change the practices, habits, and ways-of-working
→ If your systems reward old behaviors, the new culture won't stick

Most leaders stop at advocacy. 
A few model it. 
Almost none operationalize. 

This is where PE port-co cultural transformation will stall. 

* * * * * 
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Leading a PE port-co is a grind. No way around that. But what makes it harder: A dull axe.

We talk to a lot of leaders about Ascend, and the most common objection is: "Sounds great, but I'm too busy to slow down and learn."

I get it. You're too busy swinging to slow down and sharpen the axe.

But here's where this misses: 

If spending 2% of your time this year could make you even 10% sharper during the other 98%, the trade-off is a no-brainer. 

Sometimes, you've gotta slow down to go fast. 

Info on the program for PE execs is in the comments.

One of the best parts of the Ascend community we're building is the depth of wisdom among the PE operators inside. We’re going to start sharing more of it. Ya know, abundance mindset. 👊

This one comes from David Dean, an Ascend alum and one of the sharpest, most grounded PE CFOs I’ve worked with... and a heckuva good guy. Two successful exits under his belt.

We sat down and had him break down what it really takes to exit well as a PE-backed leader.

Lots of super practical advice in here that can have a big impact on your exit value. 

Full article below ↓↓

As a PE-backed executive, delivering a successful exit is part of the job—arguably one of the biggest parts. The exit is the ultimate scoreboard. It’s

Open article: Leading a Successful Exit: Lessons from a PE-Backed CFO by Dan Cremons • 9 min read

Leading a Successful Exit: Lessons from a PE-Backed CFO

Under the hood of every successful mid-market CEO are: 
 
∙ Bad ideas 
∙ Self-doubt 
∙ Uncertainty
∙ Fear of failure 
∙ Self-limiting beliefs 
∙ Imposter syndrome 
∙ Comparison to other execs
∙ Worry about how they're viewed
 
CEO, CFO, COO, C-whatever-O... 
 
We’re all just human beings with fears, uncertainties, doubts. (Present company included.) 
 
The successful ones aren't immune... 
 
They simply learn how to understand, manage and overcome these limitations.

Something I learned the hard way early in my PE career: 

Faking it is exhausting... and expensive. 

When you’re preoccupied with trying to look the part...

→ The fancy calculator
→ The Patagonia vest
→ The big words

...you’re burning energy that could be used to:

→ Sharpen your edge
→ Build real confidence
→ Double down on what makes you you

Instead, it gets spent on:

→ Managing impressions
→ Watching every word
→ Acting like someone else

And over time, the parts of you that are different (and valuable) start to fade.

Learning: The more you focus on faking it, the further you drift from your actual edge.

Lots of PE-backed companies are coming into '26 with high hopes for a breakout year. But it’s hard to drive breakout results by playing it safe. 

Wrote this article as part of a new semi-annual magazine we're publishing called The Operator's Edge. Def worth the 5 minute read as you're firming up 2026 goals. 

Check it out! ↓

TL;DR Lots of PE-backed companies come into '26 with high hopes for a breakout year. But it’s hard to drive breakout results by playing it safe. Peak 

The Stretch Zone: How to Set Goals That Grow Your People and Your Equity Value

PE folks: An unusual but powerful practice to use with your mgmt teams as you get into 2026 planning & Q1 board meetings ↓

The Power of Visualization

A lot of what I know about leading in PE came from other operators. People who'd been through it and were willing to share what worked and what didn't.

The Operator's Edge is my attempt to pay that forward. It's a semi-annual briefing for PE executives. 

Volume 1 (now live) is 10 articles covering topics like vision-setting, hiring smarter, how to prep for exit, and staying grounded when the pressure is relentless.

If you're running a PE-backed company or supporting someone who is (board, value creation, deal team, etc.), grab a copy.

Link in comments below.

A hard truth I learned the hard way early in my PE career:
Just because it looks clean on a spreadsheet doesn't mean it is IRL.

One of the first PE deals I led was a total disaster.

The return math looked good. But the business lacked something important: 

VALUE CREATION READINESS

 It wasn't positioned to make those numbers come true.

→ Leadership misalignment
→ Cultural baggage
→ Capability gaps
→ Talent gaps

It was a tough (but valuable) lesson in the importance of getting a clear read on value creation readiness BEFORE writing a big check.

Most PE firms think: "We'll own the business for 5 years. So we need a 5-year vision." But here's what they miss:

The next buyer isn't purchasing the last 5 years.
They're buying the NEXT 5 years.

The smarter play: 

Think 10+ years out.
Set a BHAG that outlasts you. 
Build toward that vision of success. 

I came across this clip in the archives from my conversation with Rob Huxtable on the topic. Roll it. 

* * * * * 

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Brentwood Associates

• Establishing the Cybersecurity Risk Management program for the Private Equity Firm with over 50 years of history and $7 billion aggregate invested in over 50 portfolio companies, ensuring alignment with SEC rules and investor expectations.
• Establishing effective and defensible cybersecurity risk management and controls for portfolio companies and assessing their successful operations in accordance with various frameworks/compliance requirements depending on the company's needs/risks (NIST CSF, DORA, NIST 800-53, ISO 27001, CIS v8, PCI DSS v4, HIPAA, NYDFS, GDPR, Various State Privacy Laws, etc.)
• Conducting cybersecurity due diligence on potential M&A activity
• ESG committee member
• Serving on Advisory Boards/Executive Steering Committees of portfolio companies

Operating Partner, CISO

Avint LLC

• Managed the leads for a portfolio of cybersecurity consulting engagements valued at over $50 million for the entire company, including strategy, engineering, governance, risk, and compliance (GRC), and program management.
• Established the Zero Trust principles and framework for the company.  Presented this at multiple conferences.
• Established Project/Program Management methodologies, both Traditional and Agile, for the company.
• Further refined reporting and monitoring processes and tools for all engagements.
• Led the Cybersecurity Maturity Model Certification (CMMC) Level One Self-assessment and preparations for Level Two external assessment
• Led vulnerability assessments using frameworks and standards such as SOX and NIST 800-53 & 171 including penetration testing with reporting and briefing to the board of directors level
• Led the Program Management portion of the ISO 9001 Audit to gain the certification for the company.

Executive Director, Cybersecurity Programs

Salvus

Specialized in Cybersecurity consulting for small to mid-sized businesses. 
•	Provided evening and weekend classes for busy professionals.  Providing in-person and remote training in cybersecurity, data analysis, ITIL, Lean Six Sigma, Project Management and Agile Project Management.
•	Provided proposal writing consultation and management to respond to government RPFs, RFIs, and RFQs for DoD, DHS, DoN, VA, NRC, and DoS.
•	Provided consulting services for companies transitioning to ITIL best practices and Agile Project Management Methodology as well as those who are looking to improve their current performance.
•	One of four experts assembled to develop the Scrum Master Certified and Agile Expert Certified curriculum.
•	Co-author of the Scrum Body of Knowledge, available for order on ScrumStudy.com.
•	Developed the Virginia Union University Lean Six Sigma Curriculum for the certification of faculty and staff.
•	Asked to develop questions for the 2016 PMP Test by the Project Management Institute.

Cybersecurity and Management Consultant

Global Commerce and Services, LLC

•	Lead the technical and program support for the DoD Enterprise Portal Service (DEPS) and the DoD365 SharePoint Online service at the Defense Information Systems Agency (DISA)
•	Lead transition efforts from the on-premises SharePoint 2013 to the cloud-based SharePoint Online IL5 environment.
•	Lead the implementation of Scrum and Agile Project Management practices
•	Developed the Request Fulfillment process
•	Lead support for Data Management, especially on the ServiceNow implementation
•	Managed communications and built relationships with internal and external customers

Senior Program Manager

Sharp Solutions, Inc.

•	Lead support for the implementation of a cybersecurity enterprise service for the Department of Homeland Security Headquarters element and Components, including tool implementation and cloud usage.
•	Lead engineering support for developing data flows to provide the Security Operations Center with data to drive incident management with Swim Lane.  Gained hands-on-keyboard experience with the tools to understand the need.
•	Lead support for certification, accreditation, and Security Compliance with the Risk Management Framework.
•	Lead support for the DHS use of Splunk to architect and integrate multiple tool inputs and data sources (Carbon Black, Cisco ISE, McAfee tools, SCCM, Symantec Tools, etc.)  into one overall management view to drive decision making and improve the cybersecurity and data analysis of the Department.
•	A Program Manager on an IDIQ contract valued at $325 million. Led efforts to pursue Task Orders from that IDIQ.
•	Leading technical support for development and implementation of cybersecurity performance metrics for the DHS CDM Program
•	Lead support for development and implementation of Software Management to drive optimization and security
•	Lead support for the development of the Cloud Computing strategy for the DHS to facilitate the modernization, consolidation, and migration of Department and Component data from data centers to FedRAMP certified cloud service providers utilizing VMware for virtual infrastructure.

Program Manager, Lead Cybersecurity Consultant

Cybersecurity is a business problem, not a technology problem.  CISOs should be transitioning from technologists who prevent breaches to corporate strategists managing business resiliency risk with a cybersecurity skillset.

Drew joined Brentwood as an Operating Partner and previously served as Executive Director of Cybersecurity Programs for a consulting firm in the Washington, D.C. area.  Drew has 15 years of cybersecurity and Program/Project Management experience. He is a published author and recognized expert in cybersecurity, project management, and IT service management. His experience includes supporting several private companies and government agencies including the Department of Defense, Department of Homeland Security, and Department of Navy. Drew has led many cybersecurity efforts including cybersecurity strategy, engineering, operations, and compliance.  Drew holds a Bachelor of Science in History from the U.S. Naval Academy and a Master of Science in Project Management from George Washington University. Drew is a Certified Information System Security Professional (CISSP) and Project Management Professional (PMP) along with holding several other professional certifications.

Views expressed do not represent those of Brentwood, its clients, or investors in the clients, or any other employees.

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