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State school kid with an art degree who wandered into private equity thirty years ago and…
Articles by Devin
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The Ghost of Software Future
The Ghost of Software Future
On software valuations, technology transitions, and why AI is a gift to lower middle market software investors. I wrote…
40 Comments -
Cooking and Investing: What I learned about private equity from learning how to cook.
Cooking and Investing: What I learned about private equity from learning how to cook.
Growing up with three brothers and young parents, our house was chaotic but fun – frequently a funhouse. I was twelve…
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Have You Become the Chief Worry Officer?
Have You Become the Chief Worry Officer?
Somewhere along the bootstrapping journey, the worries that consume successful company founders start to change. In the…
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Blessed are the Bootstrappers
Blessed are the Bootstrappers
Are you building your software company the old-fashioned way? One customer at a time? Instead of chasing VC money from…
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Why we started ParkerGale
Why we started ParkerGale
We formed ParkerGale in 2015 to create an accessible, helpful, transparent, and friendly (maybe not the first…
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Activity
6K followers
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Devin Mathews posted thisIs the arms race in PE Ops paying off? Over the past two decades, PE funds of all sizes have built out operating teams to support their portfolio companies. While it feels like the right thing to do, it’s hard to measure the results. The massive proliferation of PE Opersting role coincided with the ZIRP era of cheap debt and multiple expansion. Were returns alpha? Or beta? In the latest FunCast episode, Cass Gunderson Ziebel, Paul Stansik, and I talk about how we all got here and where we’re likely headed. Let me know if you agree. Link to YouTube in the comments, and also on your favorite podcast app.
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Devin Mathews shared thisEvery April, the team at FLEX Capital in Berlin hosts the PEC. A free, invite-only conversation among senior GPs and LPs focused on the European software buyout market. No pitches, no PowerPoint. PEC is by far the best conference of its kind. A room full of peers, off the record, honest, frank conversations about what's going on and where things are headed. They let me host a panel on private credit. There were some fireworks. I am planning to bring this format to America this fall. Comment below or message me if you want to be a part of it.
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Devin Mathews shared thisComing up on 10 years since the final close of ParkerGale I. What started as a nostalgia lap with Jim Milbery turned into a confession. Where we messed up, what most funds still get wrong, and why small is the new big. Five highlights from the new FunCast episode: Too Many Daves. PE Operating Partner roles tripled since 2020, and with that, so have value creation initiatives. Ask any portfolio CEO (off the record) how much value they're getting from the army of Daves. Most will say "not much." Little's Law. The more initiatives you push through a company at once, the less actually gets done. Pick a thing. Finish it. Move on. Sixty to ninety days. Sounds simple. But most funds can't help but pile it on. Sourcing Arms Race. Every fund now uses the same sourcing playbook. We get dozens of emails a week asking to "catch up" on our portfolio. Almost none offer anything in return. Remember, when done well, sourcing is a give business, not a get business. Add-ons: From Strategy to Crutch. Add-ons recently hit 80% of all PE deals. In software, most of these "platforms" are six companies across six tech stacks, with four roadmaps and a pro forma EBITDA number. That worked a few years ago, but that game is officially over. Nobody Stays Small. Every emerging manager promises to stick to their knitting. Then the next fund doubles. Then doubles again. StepStone found funds that more than doubled in size posted a 6-point IRR decline versus the prior fund. AUM scales better than results, but LPs keep following GPs up-market. Ten years in, we're still taking Dolly Parton's advice: "Figure out who you are and then do it on purpose." We go deep on these five lessons and five more, like: Late-cycle tourists in tech buyouts are making us all look bad. Tell us what you've learned over the past decade. Episode and Substack links in the comments.
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Devin Mathews shared thisIf you’re in Berlin next week for FLEX Capital’s PEC, let’s hang out. I’ll be talking SaaSpocalypse and private credit. And huge props to the Flex team for Benjamin Button-ing me with the 10yr old photo!
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Devin Mathews shared thisPE Lingo Bingo Ever sat in a meeting and thought: What are these people talking about? Pari passu. Quantum. Unlock. VCP. Waterfall. Clawback. QoE. Every industry has jargon. Private equity jargon is next level. So we made a game out of it. In the latest episode of the PE FunCast, Nikola Ivanisevic, Elizabeth Xu, and I break down 50 PE terms you should know (and a few you should forget). Consider it a masterclass, a survival guide, or a small act of rebellion. Print out the Bingo Cards below to play along with your friends at the next IC meeting. First one to five wins (or do they). Links to YouTube and Substack are in the comments. Drop in the comments the PE term that makes you laugh, cringe, or question your life choices.
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Devin Mathews shared thisI have never seen a time when the gap between people who know how to use a new piece of technology and people who don’t is this wide and this consequential. The gap between investors’ understanding of the situation is just as wide. Spend part of your weekend with the Ghost of Software Future and me. And tell me how you are processing the rapid change in the software industry.
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Devin Mathews shared thisParkerGale Capital sitting at the big kids’ table with Bain Capital, KKR, Alpine, and our neighbors at Shore Capital Partners. A decade of showing up for founders. Sharing what we know. And being generous when no one was looking.Devin Mathews shared thisOutside of finance, most PE firms have virtually 0 brand value beyond a few names like Bain Capital, KKR, and The Carlyle Group. Then there are thousands more funds, mostly with some combo of metal/lake/hill capital partners pitching founders the same messages: - "second bite of the apple" (aka "we can't let you retire") - "roll up our sleeves" - "patient capital" At some point, it all blurs together. So who actually stands out? Competitive advantages matter for IRR, DPI, and MOIC. But they also matter because LPs need to believe your edge is real and repeatable. The brands that actually feel distinct have something concrete behind the story: - TA Associates outclasses in sourcing - Thoma Bravo is synonymous with software - Sun Capital Partners, Inc. is your go-to for distressed deals - H.I.G. Capital leans into "hairy" deals - ParkerGale Capital is winning on content (has a podcast, YT, and blog) - Avance Investment Management and Palladium Equity Partners, LLC leverage a meaningful Hispanic angle - Infinity Constellation is the first AI-native holding company - 65 Equity Partners provides huge minority checks - Arsenal Capital Partners gives half its carry to operating partners That was the idea behind this market map: segment PE firms by actual competitive advantage, not just sector labels and AUM. There’s still a HUGE gap for PE firms that are more content-forward, AI-forward, and better at building genuine ecosystems around LPs, talent, and partnerships. A handful of the logos on here are Scend customers. The market map was also generated by Scend. #privateequity #pe #dealmaking #privatecapital #brandstrategy #contentmarketing #ai #sourcing #growthstrategy #Scend
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Devin Mathews shared thisCharles Dickens and Citrini Research walk into an IC meeting. Dickens brings the ghosts. Citrini brings the shorts. One tells you what happens if you don't adapt. The other bets it's already too late. Every major platform shift in the last 50 years came with a credible argument that software incumbents were finished. Mainframes. Client-Server. Internet. iPhone. Cloud. Now the Ghost is AI. Every time, the obituaries were written too early. Every time, most patients adapted. Many thrived. I wrote 10,000 words for my LPs on why this time isn't different and why AI is the gift lower-middle-market software investors have been waiting for. Now I'm sharing it publicly. It's called The Ghost of Software Future. Lemme know what you think.
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Devin Mathews shared thisYou should start your own private equity firm. Today. But how? 12 years ago, when my partners and I started ParkerGale Capital, we couldn't find a field guide. So we built one. And now it's yours. For free. Check out our 5-part Substack series, called PE 101. - Starting a firm - Raising a fund - Buying a company - Improving a company - Selling a company As always, you can find all this on YouTube, Spotify, and Apple, too. Just look for The Private Equity FunCast where all fresh produce is sold. And subscribe where you are over there, cuz that's the only way other people find it. Link in the comments
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Devin Mathews liked thisDevin Mathews liked thisSo last week I did a thing. After nearly 33 years with William Blair & Company, I am officially signing off. Looking back, I realize how lucky I’ve been. People often ask about the challenges of this industry, but at a firm like Blair, doing the right thing is easy, it’s woven into the DNA of the place and modeled by its leaders every day, also science is real. To my Compliance crew: thank you for the friendship, camaraderie and the commitment. It’s been an honor to serve alongside you. To the FINRA (NASD) Fighting 75th, has it been that long? To Kathleen, Mark, Art, Cunningham and Cissie: thank you for the wisdom and for knowing exactly when to tell me to shut up. I wouldn't have made it without you. To the decades of analyst classes and employees that have passed through our hallowed halls: the honor was truly mine. Many in those classes have gone on to become senior bankers and captains in their fields, which doesn’t happen at lesser firms. From the cheer captains to those in the bleachers, you were always a sky full of stars. Thank you for the late-night hijinks, for Bcc’ing me on emails to stay out of trouble, for calling yourselves “tools” so I didn’t have to, and for taking the grief I threw your way over your college football teams. Thank you for sharing a portion of your lives with me. As I move into this next phase, I think of the words of Avicii: "One day you'll leave this world behind, so live a life you will remember." Thank you, William Blair, for giving me a career worth remembering. To my family: thank you for being my rock. I’m officially home now, which means my retirement has just become your full-time job. I am, quite simply, the luckiest guy around.
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Devin Mathews liked thisDevin Mathews liked thisToday was my last day with 3M. In 2006 3M was the first and a foundational client of my consulting practice (HJM Advisors). In 2017 I joined the company full time. Over the last 20 years I have had the opportunity to work with so many amazingly talented individuals - good, smart, and hard working. I’ve also made so many wonderful friends. While I look forward to new and exciting opportunities on the horizon, I wish them all the very best for the future.
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Devin Mathews liked thisDevin Mathews liked thisThe more we build with AI, the more interesting the shift becomes. I’m seeing a lot more demos. A lot more prototypes. A lot more “look what we built in a day” moments. Well that’s exciting. But demos are not production. It’s easy to build something cool when you don’t have to worry about scale, security, observability, supportability, cost, or what happens when real customers start using it. At some point, we all have to pay the piper. That is when the real questions show up: Can it scale? Can it be monitored?Can it send the right signals back? Can it be secured? Can it be supported? Can it actually live in production? Without real guardrails around what goes into production, the problem only compounds. Don’t get me wrong, I’m a big believer in AI-driven SDLC, agentic development, and code generation. But I’m an even bigger believer in solid engineering. The job now is finding the sweet spot between speed and discipline. Move faster, yes. But don’t confuse a great demo with a production-grade product. We are all still early in figuring this out and we will be early stage for a bit however, we need to keep building.
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Education
Publications
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The 7 Deadly Sins of Private Equity
Business Insider
See publicationAvoid temptation when raising and investing private equity.
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'I Have a Meeting in Westchester' and Other Essential Code Words for PE Newbies
PEHUB
See publicationThe code words you need to know before starting your private equity career.
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How to Avoid The Venture Capital Trap
Fortune.com
See publicationYou might think the only path to building a successful startup is to learn to code, drop out of college, raise $50 million from venture capital firms, and sell to Google. That's not the case, at all.
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Have You Become the Chief Worry Officer
Fortune.com
See publicationOnce your business reaches a point of stability, it's easy to find yourself worrying about more distant threats. How to break the habit.
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Attivo Partners
Board reporting isn’t just a requirement of venture-backed growth: it’s one of the most powerful tools founders have to drive alignment and better decision-making. In his latest CFO piece, Mike Batesole, CPA, CMA explains how board reports can evolve from tactical updates into a strategic leadership exercise. He outlines what effective board reporting looks like at each growth stage and how intentional structure leads to more focused discussions, clearer priorities, and stronger outcomes. Read the full piece here: https://lnkd.in/eNVdxuu8 Preparing for an upcoming board meeting? Attivo helps founders create decision-ready board materials and offers CEO support. #AttivoPartners #BoardReporting #FractionalCFO #StartupFinance #FounderLeadership
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Accordion
Last week at PEI's Operating Partners Forum in New York, our own Mitchel Nakken led a panel with TPG leaders on how top CFOs and PE operating partners align. The discussion covered many of the themes we focus on with clients including how the PE-backed CFO's role has evolved, how to scale transformation while sustaining performance, and how operating partners should act as connective tissue for CFOs.
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Riveron
Private equity wins aren’t built on dealmaking alone. Riveron National Private Equity Leader Nate Heeren explains how operational discipline and CFO leadership are redefining value creation in his latest Forbes feature. Read more from Nate in Forbes Finance Council: https://lnkd.in/ggwUxQBF #Riveron #ForbesFinanceCouncil #PrivateEquity #ValueCreation #Operations
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The Circle by Founders Circle Capital
The growth-stage CFO role is uniquely isolating. As you scale toward IPO, you're expected to deliver operational precision while managing board scrutiny, investor expectations, and rapid organizational change. Every quarter can feel like you're being re-interviewed for your job. The Circle founder, Mark Dempster, joined Megan Weis, CPA, MBA on the CFO Weekly podcast to unpack why peer infrastructure has become essential for CFOs navigating this stage. In the conversation, he talks through: • The hidden isolation of the CFO seat • Why vulnerability among peers is a strategic advantage • How shared “scar tissue” reshapes risk tolerance Listen here: 🎧 Apple Podcasts: https://lnkd.in/e4MHz6px 🎧 YouTube: https://lnkd.in/eiBz6fdF 🎧 Spotify: https://lnkd.in/ebnycBi3 The Circle by Founders Circle Capital is a private community built specifically for growth-stage CFOs leading through scale. If you’re in the seat, you don’t have to navigate it alone. Interested in learning more about membership? Explore here👇 https://lnkd.in/g-2Ygves
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The SaaS Academy
Transformations take capital—and Markup AI is no exception. In this episode of The SaaS CFO Podcast, Matt Blumberg (CEO @ Markup AI) shares details on their recently announced $27M financing, a mix of fresh equity from existing PE investors, debt refinancing, and strategic angel participation. This funding fuels a full reinvention of the business—including a major structural shift from a German GmbH to a newly domiciled U.S. entity. A great discussion on capital strategy, ownership, and rebuilding a company for its next stage of scale. Episode 218 is now available—links down below 👇 YouTube: https://lnkd.in/gz2i558r Apple: https://rpb.li/tgVFdD Spotify: https://rpb.li/7pwzP5xca #SaaS #CapitalRaising #PrivateEquity #SaaSPodcast #StartupFunding
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Oaklyn Consulting
In many M&A conversations, the real obstacle isn’t valuation. It’s the internal assets no one’s talking about, divisions that aren’t scaling, customer segments that aren’t delivering, or leadership alignment that’s fraying. I joined the From Angel to Exit podcast to discuss how founders can use moments like this as turning points, not dead ends. If your company feels stuck between readiness and reality, give it a listen. You can find the full episode at the links below: Apple Podcast Episode Link: https://lnkd.in/eTrvpx6S YouTube Episode Link: https://lnkd.in/eJEaZJGM From Angel To Exit Website: https://lnkd.in/eKV2je4s #strategy #businessacquisition #CapitalRaising
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streamOS
The Accordion team has put together a beautifully designed survey that belies a really ugly disconnect between PE expectations and CFO execution. 98% of PE sponsors have *ahem* asked their CFOs to prioritize the use of AI in the finance function - with only 4% of CFOs reporting that they've managed to implement AI broadly. That's a pretty sizable delta. Reasons are myriad, but in the end PE and investors in general hold both carrot and stick. https://lnkd.in/egefv2Dr
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Trivest Partners
Great perspective from FP&A Tomorrow and our own Jamie Lukaszewski, Director of Financial Operations here at Trivest, on how PE really works with FP&A teams. The best FP&A leaders don’t just report the numbers — they build forward-looking systems that drive true value creation. #FPA #ValueCreation
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