Private Equity Data Guy

Graeme Crawford
  • 5.0 (3)
  • BUSINESS

Private equity meets data. Conversations with deal teams, operating partners, and portfolio company leaders about the data problems that kill deals, slow exits, and destroy value. Hosted by Graeme Crawford, founder of Crawford McMillan. 20 years leading data programs at Fortune 100 companies. Now helping PE-backed companies fix data before exits so the numbers hold up under scrutiny. New episodes cover diligence red flags, value creation playbooks, and the real stories behind successful (and failed) transactions.

  1. This Is How He Turned Agency Ownership Into a Video Game

    5D AGO

    This Is How He Turned Agency Ownership Into a Video Game

    Peter Kang built Barrel into a cash-flowing agency over fifteen years before he ever touched a deal. That patient foundation is what separates Barrel Holdings from a traditional PE firm. No fund, no management fees, no forced exit timeline. Just cash flows reinvested into acquiring good businesses at fair prices, with SBA financing doing the heavy lifting until the flywheel grows strong enough to need less leverage. We talk through what Peter looks for beyond the obvious numbers, including client retention, average tenure, concentration risk, and whether there is real leadership depth below the founder. We get into the Bolster story, the design agency he incubated, loved, and had to walk away from when he realized he was the only reason it had any business at all. And we get into how AI is changing what agencies can deliver, what clients are willing to pay, and how the hourly model is holding on by a thread in a world that rewards output over time. TIMESTAMPS [0:00] Peter Kang and Barrel Holdings [2:02] Holdco Tycoon game origin [5:18] Holdco structure vs PE fund [8:31] Price, leverage, sourcing lessons [16:18] AI reshaping agency work [21:05] What data matters in acquisitions [23:01] Culture risk and Bolster story [30:26] Documenting failures publicly KEY TAKEAWAYS Buying discipline matters more than deal flow. Overpaying is one of the fastest ways to get into trouble, and time pressure only makes it worse. Client retention and average tenure tell you more about an agency than revenue growth. Concentration risk is a red flag worth walking away from. Culture is not a feeling. It is the standards a leadership team enforces and models every day. When those standards clash post-acquisition, good people leave. Publishing failures is a sourcing strategy. Trust is built through transparency, and founders looking to exit remember who showed up honestly. AI is not replacing agencies. It is raising the standard for speed and output, and the pricing models that survive will be the ones tied to value, not hours. COMPANIES MENTIONED Barrel Barrel Holdings Agency Habits Bolster WEBSITES MENTIONED peterkang.com barrel-holdings.com https://www.linkedin.com/in/peterkang34/ GUEST INFORMATION Peter Kang co-founded Barrel in 2006 and spent two decades building it into the foundation for Barrel Holdings, a portfolio of digital agencies across e-commerce, Amazon, B2B marketing, and home services. He published The Holdco Guide and created the Holdco Tycoon game to share the capital allocation lessons he learned the hard way. Peter writes openly about wins and failures and runs Barrel Holdings with a decentralized, operator-led model.

    48 min

  2. APR 17

    What PE Buyers Find When They Actually Look at Your Data

    In this episode, I sat down with Derek Sather, CRO at KKR-backed Education Perfect, to talk about what actually happens when someone with deep systems thinking and revenue architecture experience steps inside a PE portfolio company. Derek breaks down what it means to move from managing a pipeline to underwriting revenue, and why that shift matters more now than ever before. We get into the real cost of messy data during diligence, what buyers are actually looking for when they dig into your revenue numbers, and why AI will amplify your chaos just as fast as it amplifies your clarity. If you are building toward an exit or trying to make your revenue engine defensible, this one is worth your full attention. [00:01:42] - Derek's background and career path [00:06:16] - What the data looked like going in [00:13:31] - Revenue numbers and diligence breakdowns [00:17:19] - Building credibility one metric at a time [00:22:23] - Demand architecture and the new CRO role [00:29:44] - What buyers look for before an exit [00:34:22] - Retention vs acquisition and compounding growth [00:39:38] - AI, clean data, and the new PE playbook Guest Information Derek Sather is an MIT-educated systems thinker and current CRO at Education Perfect, a KKR-backed edtech platform based in Sydney, Australia. He spent six years at Winning by Design helping over 600 software companies engineer predictable revenue. Find him on LinkedIn. Companies Mentioned Education Perfect KKR Winning by Design Capital One IBM Uber Websites Mentioned https://www.linkedin.com/in/dereksather Key Takeaways One metric, one owner, one logic chain. That is how credibility gets built. A messy revenue engine does not get fixed by AI. It gets scaled into more confusion. Revenue quality is the asset. Not just revenue growth.

    44 min
  3. Is your Data telling you the right story?

    APR 9

    Is your Data telling you the right story?

    Holli Moeini spent 35 years as a CFO scaling companies through acquisitions before leaving corporate to help founders protect their value when going up against PE buyers. Her book, Find the Missing Millions in M&A, breaks down the five moments in every deal where money moves toward you or away from you. In this episode, she maps out each one and explains what sellers can do before they ever get to the table. The conversation gets into the financial story, working capital, diligence, earn outs, and integration. Each one is a place where the unprepared seller loses. The ones who walk away with the most are the ones who treat their data and accounting as front office functions, not back office overhead. [00:00| You cannot go it alone [04:55| Five crime scenes in every deal [07:15| Cleaner data, better multiple [11:41| Working capital costs millions [20:57| Earn out clarity control cadence [25:29| Integration starts before close [29:02| Data as a front office function [41:49| Run it like you will sell Guest Information Holli Moeini is a CPA and M&A advisor with over 35 years in finance. She spent her career as a CFO scaling companies from $30M to $200M through acquisitions. She now works with founders and sellers preparing for PE transactions. Companies Mentioned IBM Capital One Barnes and Noble Amazon Websites Mentioned https://hollimoeini.com/

    48 min

  4. APR 2

    Private Equity Is a Talent Business, Not a Finance Business

    Tim Schulte leads value creation at Council Capital, a healthcare-focused PE firm in Nashville. He spent years at Vista Equity Partners before building something different at Counsel. In this conversation, we get into why the playbook model breaks down across a diverse portfolio, what a toolkit approach actually looks like in practice, and what AI is doing to the work of value creation right now. We get specific on data infrastructure, change management, and why the people question determines whether any of this works. Tim's view on AI is one I share: the tools are getting better fast, the value still sits in implementation and adoption. We cover the state of PE returns, what the industry has to do to justify its position going forward, and how Council Capital is building real operational capability at the lower middle market level. [00:01:53] Tim's path into private equity [00:06:01] What Vista Equity got right [00:10:08] Toolkits vs playbooks explained [00:14:06] Data infrastructure across diverse portfolios [00:19:44] AI and the toolkit build process [00:26:14] Recommending AI across portfolio companies [00:32:47] PE history and what comes next [00:39:37] Where the industry is heading Key Takeaways The playbook model breaks down when portfolio companies are diverse. Toolkits that operators choose to use work better than mandated processes. Data strategy has to serve the operating team first. If the PE firm pulls data that operators don't use, the problem is alignment, not data. AI saves time on framework creation. The value is still in getting people to change how they work. Companies Mentioned Council CapitalVista Equity PartnersRampAnthropicOpenAIBrookdale Senior LivingCignaKrogerUniversity of Chicago Websites Mentioned https://councilcapital.com/ Guest Information Please provide details about the guest who will be featured in the episode. Guest's Full Name Tim Schulte Company / Organization Council Capital Website or Main Page Empty Guest Social Media Links https://councilcapital.com/

    41 min
  5. What PE Gets Right That Corporate America Never Will

    MAR 26

    What PE Gets Right That Corporate America Never Will

    Ryan Krook has spent his career at the intersection of data and operations, working inside companies like Uber, Shopify, and McKinsey before founding Pareto Apps. In this episode, we get into what it actually looks like to walk into a mid-market PE portfolio company that has never taken data seriously, and what to do about it. Ryan brings a perspective I don't hear often: he has sat on the LP side, worked as an outside consultant, and now operates hands-on inside the companies fixing the problems that matter most at exit. What stood out to me most was Ryan's take on starting small. Not small as in unambitious, but small as in disciplined. Get one reliable metric. Build from there. That approach, rooted in the Pareto principle, is how you create real operational leverage without pulling people away from the work that actually drives the business. We also got into the risks that come with vibe-coded apps, AI without data governance, and the version control nightmare that happens when everyone builds their own tool. Timestamps [00:02:09] - Ryan's path into data [00:07:49] - Working inside PE at McKinsey [00:15:53] - Mid-market companies and data gaps [00:21:52] - Data governance and why it matters [00:25:09] - Where to start with data investment [00:30:51] - Iterative builds and fast delivery [00:38:00] - Vibe coding risks in enterprise [00:42:04] - AI capabilities, a 1 to 10 take Guest Information Ryan Krook is the founder of Pareto Apps, a firm that builds bespoke data and AI solutions for PE-backed portfolio companies and early-stage startups. He previously held roles at Ontario Teachers' Pension Plan, McKinsey, Uber, and Shopify. Ryan is based in Canada and focuses on getting companies to a place where their data is reliable enough to actually use. Companies Mentioned Pareto AppsOntario Teachers' Pension PlanMcKinseyUberShopifyBowellSnowflakeBolt Websites Mentioned paretoaps.coLinkedIn Key Takeaways Start with one reliable metric before building anything largerData governance is what makes AI outputs trustworthyPE-backed companies move faster because everyone is aligned around the same exit timelineVibe-coded apps carry the same version control risks as unmanaged spreadsheetsThe barrier to standing up solid data infrastructure has dropped significantly in the last few years

    52 min
  6. How this company lost $2.8M due to three mismatched numbers

    MAR 12

    How this company lost $2.8M due to three mismatched numbers

    Greg Hood has spent over 20 years as a finance executive inside Canadian and US fintechs and financial services firms. He built Sky Site Analytics to help PE firms, sell-side M&A advisors, and high-growth companies fix the data layer before buyers find it first. We cover the dirty data discount, what actually breaks during exit, and why the back office is always the last to get the budget it needs. If you have ever sat across from a buy-side team watching trust drain out of a room because three reports show three different revenue numbers, this conversation is for you. Greg and I have worked in the same trenches long enough to know that the data problem is almost never a technology problem. It is a process problem wearing a technology disguise. TimestampsChapters: 00:04 - Challenges in Product Management03:37 - The Evolution of Data in Finance09:12 - The Importance of Data Quality in Finance23:16 - The Importance of Accurate Financial Data Reporting29:23 - The Impact of AI on Business Practices36:33 - The Value of Data in Business43:49 - The Valuation of Data as an Intangible Asset GuestGreg Hood is a CPA and CMA who held one of the first Chief Data Officer roles earned by a CPA. He founded Sky Site Analytics, a Toronto-based consultancy that works with PE firms and high-growth companies on finance data infrastructure and exit readiness. His team won Most Innovative Finance Department while at Q Trade, an online brokerage, where they cut a two-and-a-half-day close process down to under two hours. Companies MentionedSky Site AnalyticsQ TradeKunaiParamount CommerceCampfire (AI-first ERP)QuickBooksNetSuiteSnowflakeDatabricksAnthropic (Claude) Websites MentionedSky Site AnalyticsGreg Hood on LinkedIn Key TakeawaysInconsistent revenue numbers across reports can cost millions in exit valuation, not because the business is bad but because trust is gone.The data layer is routinely skipped during due diligence, and that gap is getting more expensive as data rooms grow from 30 documents to over 300.First-party data can be a monetizable asset, but quality and uniqueness determine value. If your data looks like everyone else's, it is not worth what you think.

    49 min
  7. The Data Problem That Kills PE Exit Multiples

    MAR 6

    The Data Problem That Kills PE Exit Multiples

    Shota Ishii joined me on The PE Data Guy to talk about what happens when PE-backed manufacturers cannot answer a basic question: which products are actually making money? He has spent two decades building systems that give companies a clear picture of where their cash goes, and we got into why that gap exists and what it takes to close it. We covered working capital, data architecture, and what mid-market companies need to do right now to get their data in order before AI can do anything useful for them. Shota shared an example of a $400 million metal company that found $80 million in working capital improvements once they had the right transaction-level visibility. Chapters: 00:00 - Understanding Capital Efficiency06:42 - The Journey to Becoming a Robo CFO20:55 - Amazonifying Legacy Industries: The Need for Real-Time Data31:51 - The Importance of Data Strategy in Mid-Market Companies35:18 - The Future of AI in Mid-Market Companies Guest InformationShota Ishii is the founder of Proximo Tech, where he works with PE-backed manufacturers on capital efficiency and working capital. He studied applied physics and AI and has a background in quantitative finance, hedge funds, and corporate innovation. He is based in Japan and can be found on LinkedIn. Companies MentionedProximo TechMoody'sBlackstone CreditAmazonSnowflakeDatabricksAWSGoogle CloudSalesforceOpenAI Websites MentionedProximo TechLinkedInSnowflakeDatabricksAWSGoogle Cloud Key TakeawaysClean, granular data at the transaction level is the foundation for improving working capital.The cost of not building a data platform grows over time as competitors who do build one move faster.Data is a company asset. Without structure and governance around it, AI cannot make use of it.Mid-market companies often underestimate how affordable modern data tools actually are.

    45 min
  8. Why Your PE AI Program Is Already Failing

    FEB 27

    Why Your PE AI Program Is Already Failing

    Shawn Olds spent two decades building AI companies and advising PE firms on what actually produces returns from the technology. He went from the 82nd Airborne to West Point computer science to co-founding Boodle Box, and along the way he has worked with over 200 companies on AI adoption. The number that should make every operating partner stop: over 80% of AI programs in portfolio companies fail. Not because the technology breaks. Because of decisions made before a single tool is ever deployed. Shawn and I covered why context engineering has replaced prompt engineering, why CEO backing is the one variable that separates companies getting real ROI from those just gaining productivity, and how PE firms can use data scientists during due diligence to surface hidden EBITDA before they close a deal. He also walked through real examples from the security industry that show how unstructured data already sitting inside a company can be turned into millions in annual savings without purchasing a single new tool. Chapters: 00:07 - The Role of AI in Prompt Creation02:04 - The Journey into AI Consulting11:08 - Empowering Innovation in AI Adoption24:14 - Harnessing AI in Business: Practical Applications29:39 - The Role of AI in Enhancing Business Processes37:41 - Starting with AI: Understanding the Journey Guest Information Shawn Olds is an AI strategist and co-founder of Boodle Box, a platform that brings multiple AI models into one collaborative workspace. He studied computer science at West Point and served in the U.S. Army's 82nd Airborne before spending two decades building technology companies across the United States, the Middle East, and Africa. He now advises PE firms and portfolio company CEOs on practical AI adoption that produces measurable business results. Companies Mentioned Boodle BoxMcKinseyBainBCGPwCMIT7-ElevenHire AlignedZero Prostate Cancer Foundation Websites Mentioned NotebookLMChatGPTClaudeGeminiPerplexityLinkedIn

    41 min
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Ratings & Reviews

5
out of 5
3 Ratings

About

Private equity meets data. Conversations with deal teams, operating partners, and portfolio company leaders about the data problems that kill deals, slow exits, and destroy value. Hosted by Graeme Crawford, founder of Crawford McMillan. 20 years leading data programs at Fortune 100 companies. Now helping PE-backed companies fix data before exits so the numbers hold up under scrutiny. New episodes cover diligence red flags, value creation playbooks, and the real stories behind successful (and failed) transactions.

Information

  • Creator
    Graeme Crawford
  • Years Active
    2025 - 2026
  • Episodes
    34
  • Rating
    Clean
  • Copyright
    © Copyright 2026 Graeme Crawford
  • Show Website
    Private Equity Data Guy