Episodi

  • I Drove 3 Hours to See Inside a $3B PEO Acquirer (Here's What I Found)

    I Drove 3 Hours to See Inside a $3B PEO Acquirer (Here's What I Found)
    Apr 17 2026
    I drove three hours. No agenda, no idea what I was walking into to spend half a day inside Vensure Employer Services headquarters. What I saw was nothing like what I expected. 105 acquisitions. 8 deals in legal. 50 in the pipeline. $750M in revenue and still raising capital. This episode is the closest thing to a behind-the- scenes tour of the most aggressive PEO acquirer in the country and I'm sharing everything: how they structure deals, what they actually pay, why they don't force platform migrations, their AI client churn prediction tool that's 80% accurate, and what this means if you own a payroll bureau or PEO and are even remotely thinking about what comes next. This is not a sponsored episode. I told Alex Campos I wouldn't be a shill. This is my unbiased take after a 250-slide deck and a full facility tour. Subscribe for weekly intel on running and growing a payroll business: https://www.youtube.com/@payrollinpod Join the newsletter: https://www.payrollinpodcast.com/ ⏰ TIMESTAMPS: 00:00 — Why I drove 3 hours on a 15-minute phone call 02:57 — What I thought they wanted (I was wrong) 05:21 — The current Vensure scoreboard: 105 deals and counting 07:37 — How the deal structure actually works (80/20 split explained) 13:36 — Inside the 1,200-task acquisition system 18:03 — The AI tool predicting client churn with 80% accuracy 24:36 — Should you sell? The only thing I'll say about that. #PEO #PayrollBusiness #BusinessAcquisition #SmallBusiness #HRTech 📧 GET THE INSIDER NEWSLETTER Weekly strategies for scaling your payroll bureau (1,000+ leaders subscribed) → https://www.payrollinpodcast.com/ 🎯 THIS WEEK'S RESOURCE: 💼Three Keys to Expand Your Payroll Business. Learn the top tactics to scale and grow your payroll company https://youtu.be/6aW8RmVj8OE 💡 SCALE YOUR BUREAU WITH OUR HELP: 1️⃣ Add PEO Services - New revenue stream without new clients → Learn more: https://www.guhroo.co/partners/ 2️⃣ Hire Virtual Assistants - Scale operations at 70% less cost → https://www.outsourcedscale.com/ 3️⃣ Marketing That Works - Get the system we use → https://underdogdigital.co/ 🔔 SUBSCRIBE for weekly payroll growth strategies: → Hit the bell to never miss an episode 💬 CONNECT WITH MATT: LinkedIn: https://www.linkedin.com/in/mattvaadi Facebook Group: https://www.facebook.com/groups/payrollinnovation #payroll #payrollservices #bureauowner How do payroll company acquisitions work? What is the 80/20 deal structure in payroll acquisitions? How do PEO acquisitions work? What happens when you sell your payroll business? How much are payroll companies worth when selling? How long does it take to sell a payroll company? What do buyers look for in a payroll business? Should I sell my payroll company or keep it? How are PEO companies growing through acquisitions? Why is the payroll industry consolidating?
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    26 min
  • The PEO Industry Lost 40% of Its Players. What's Next?

    The PEO Industry Lost 40% of Its Players. What's Next?
    Mar 26 2026
    📧 Get weekly payroll bureau growth strategies (1,000+ leaders subscribed): → https://www.payrollinpodcast.com/Matt recently joined Pete A. Tiliakos and Julie Fernandez on the HR & Payroll 2.0 Podcast for a thoughtful conversation on the future of HR, payroll, and PEO services.In this episode, they discuss:• Matt’s journey into the payroll and HR space• The current state of PEO consolidation and market pressure• Why the SMB market is changing and what buyers want today• The growing divide between tech-first solutions and service-first providers• How niche specialization can create a major competitive advantage• The rise of embedded payroll and what it could mean for the industry• How AI is influencing HR and payroll tools, pricing, and buyer expectations• Why companies should focus on solving real pain points instead of chasing shiny featuresFrom go-to-market strategy to the realities of serving small businesses, this episode is full of practical insights for payroll providers, HR leaders, and anyone watching the future of workforce technology.⏰ *TIMESTAMPS:*0:00 Intro01:04 Matt’s background and how he got into the industry03:20 Why people stay in payroll and HR longer than expected06:43 What’s exciting (and concerning) in today’s SMB market08:38 The rise of the DIY buyer and changing buying behavior11:32 The reality of competition and “everything looking the same”14:40 Why niche payroll providers are winning (and scaling faster)16:53 Private equity’s role in reshaping the PEO industry18:52 The big stat: PEOs down ~40% due to consolidation21:13 Will consolidation continue into the future?22:43 Enterprise players entering the space (Workday, Insperity)26:31 Overcrowding, trust, and how buyers actually choose providers30:22 Centers of influence: CPAs, brokers, and referral ecosystems32:35 The overlooked opportunity with consultants and fractional leaders39:27 Embedded payroll: hype vs reality44:34 AI in payroll: what’s real today and what’s coming next📧 *GET THE INSIDER NEWSLETTER*Weekly strategies for scaling your payroll bureau (1,000+ leaders subscribed)→ https://www.payrollinpodcast.com/🎯 *THIS WEEK'S RESOURCE:*📄 Take your payroll company to the next level. Get expert strategies for rapid growth!https://go.guhroo.co/payroll-company-growth💡 *SCALE YOUR BUREAU WITH OUR HELP:*1️⃣ *Add PEO Services* - New revenue stream without new clients→ Learn more: https://www.guhroo.co/partners/2️⃣ *Hire Virtual Assistants* - Scale operations at 70% less cost→ https://www.outsourcedscale.com/3️⃣ *Marketing That Works* - Get the system we use→ https://underdogdigital.co/🔔 *SUBSCRIBE for weekly payroll growth strategies:*→ Hit the bell to never miss an episode💬 *CONNECT WITH MATT:*LinkedIn: https://www.linkedin.com/in/mattvaadiFacebook Group: https://www.facebook.com/groups/payrollinnovation👉 *TODAY'S GUEST:*→ Pete Tiliakos, HR Tech Analyst & Strategic Advisorhttps://www.linkedin.com/in/petetiliakos/→ Julie Fernandez, Global HR Advisory Leadhttps://www.linkedin.com/in/petetiliakos/#payroll #payrollservices #bureauowner What is a PEO and how does it workHow do small businesses manage payrollWhat is the best payroll service for small businessHow to choose HR softwareWhat is HCM softwareHow to grow a small businessHow to manage employees effectivelyWhat do small businesses struggle with mostHow to scale a businessIs AI replacing HR jobsHow is AI changing payrollWhat to look for in a payroll provider
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    59 min
  • The Advice That's Killing Your Business (Focus vs. Everything)

    The Advice That's Killing Your Business (Focus vs. Everything)
    Mar 13 2026
    📧 Get weekly payroll bureau growth strategies (1,000+ leaders subscribed): → https://www.payrollinpodcast.com/ "Focus on one thing" is the most repeated business advice on the internet right now. It's also the wrong first step for most entrepreneurs. Matt Vaadi and Chris Clark make the case that unfocused experimentation isn't a detour, it's the path. From worm farms and deodorant blogs to a $5.3M company built from a Google spreadsheet, they walk through the shots on goal you have to take before you earn the right to focus. Inside this episode: Why the quantity group always beats the quality group (the ceramics study) The 3 signals that tell you it's time to stop experimenting and lock in How Underdog Digital went from a marketing side project to doubling year over year Peter Levels: 12 startups in 12 months—one became $5.3M/year with 2 people The ELF framework for identifying your best niche (Easy, Lucrative, Fun) What product-market fit actually feels like when you finally hit it If you've been told to "just focus" before you've even found what's working, this episode is for you. ⏰ TIMESTAMPS: 0:00 Payrollin’ intro 1:32 Focus vs. shots on goal 2:31 Chris Clark’s first online projects 5:20 Favorite wrestler and early internet memories 6:30 What Chris does today 8:42 Matt’s entrepreneurial journey begins 9:14 Selling worms for 25 cents 10:32 Yankees ticket flipping, landscaping, and early hustles 11:49 From ERG Payroll to multiple businesses 12:15 Killing a business line when product market fit fades 12:58 How Underdog found its winning model 14:53 Unlimited marketing for $2,995/month 16:45 Underdog doubled and why delivery matters 17:25 Why failed projects still matter 18:17 Justin Welsh and quitting successful things 19:35 The deodorant blog story 21:25 Outsource Scale ad 22:37 Peter Levels and 12 startups in 12 months 24:09 A $5.3M business with 2 people 25:43 Why abandoned projects still teach you something 27:12 When to pull back vs. stick with it 29:19 How Matt recognized real product market fit 30:43 Why niching down still matters 31:49 Why broad messaging doesn’t work 33:03 Cold email: broad pitch vs. niche pitch 34:05 The power of one strong integration 35:01 Why small niches can still be huge 35:28 Why industry expertise commands a premium 36:37 When to stop experimenting and focus 37:32 Why Underdog Sports exists 39:52 The “slow” lesson from Matt’s daughter 40:46 The ceramics story: quantity beats perfection 42:29 Is there an entrepreneurial gene? 43:21 Intuition vs. data in business 44:18 Why failure in public doesn’t matter 44:56 Final thoughts and subscribe 📧 *GET THE INSIDER NEWSLETTER* Weekly strategies for scaling your payroll bureau (1,000+ leaders subscribed) → https://www.payrollinpodcast.com/ 🎯 *THIS WEEK'S RESOURCE:* 📄 Payroll Sales Playbook → https://www.payrollinpodcast.com 💡 *SCALE YOUR BUREAU WITH OUR HELP:* 1️⃣ *Add PEO Services* - New revenue stream without new clients → Learn more: https://www.guhroo.co/partners/ 2️⃣ *Hire Virtual Assistants* - Scale operations at 70% less cost → https://www.outsourcedscale.com/ 3️⃣ *Marketing That Works* - Get the system we use → https://underdogdigital.co/ 🔔 *SUBSCRIBE for weekly payroll growth strategies:* → Hit the bell to never miss an episode 💬 *CONNECT WITH MATT:* LinkedIn: https://www.linkedin.com/in/mattvaadi Facebook Group: https://www.facebook.com/groups/payrollinnovation 👉 *TODAY'S GUEST:* → Chris Clark, Marketing Coach at Underdog Sports → Chris Clark is the Marketing Coach of Underdog Digital, helping sports brands and growing businesses scale through content and AI-driven systems. With 15+ years in sports media and marketing, Chris now focuses on building practical AI workflows that drive real revenue. #payroll #payrollservices #bureauowner Should you niche down when starting a business? How do you choose a niche for your business? How do you find product market fit?
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    46 min
  • What is Vibe Coding? How to Generate Leads In One Hour for Your Business (with Chris Clark)

    What is Vibe Coding? How to Generate Leads In One Hour for Your Business (with Chris Clark)
    Mar 4 2026
    📧 Get weekly payroll bureau growth strategies (1,000+ leaders subscribed): → https://www.payrollinpodcast.com/ In this episode, Chris walks through how he builds custom AI-powered sales systems without hiring developers or waiting months for software builds. Using tools like Claude and Lovable, he created a functional virtual SDR and lead engine in under an hour. Inside this episode, you’ll see: How to build custom business software without being a developer How to scrape and qualify leads using AI How to connect tools into automated sales workflows How Underdog Digital builds CRM tools tailored to client need Why founders should learn vibe coding now The balance between AI automation and human oversight If you’re a founder, marketer, or sales leader who’s tired of duct-taping software together, this episode will show you how to start building exactly what your business needs. ⏰ **TIMESTAMPS:** 0:00 Intro 2:13 Why Claude is our AI stack 4:14 AI built a Facebook ad that booked a customer 6:46 Why AI still needs human oversight 10:35 Using AI to find information faster 13:13 Analyzing support tickets with Claude 17:25 Mining 90,000 tickets for insights 21:15 Using AI to analyze YouTube performance 24:44 How to prompt AI properly 29:55 Turning PDFs into instant answers 35:52 Building a virtual SDR with Lovable 38:20 Scraping and enriching leads automatically 42:41 Build what you need nothing more 48:19 Why founders should be learning this 50:38 Final thoughts 📧 *GET THE INSIDER NEWSLETTER* Weekly strategies for scaling your payroll bureau (1,000+ leaders subscribed) → https://www.payrollinpodcast.com/ 🎯 *THIS WEEK'S RESOURCE:* 📄 Take your payroll company to the next level. Get expert strategies for rapid growth! https://go.guhroo.co/payroll-company-growth 💡 *SCALE YOUR BUREAU WITH OUR HELP:* 1️⃣ *Add PEO Services* - New revenue stream without new clients → Learn more: https://www.guhroo.co/partners/ 2️⃣ *Hire Virtual Assistants* - Scale operations at 70% less cost → https://www.outsourcedscale.com/ 3️⃣ *Marketing That Works* - Get the system we use → https://underdogdigital.co/ 🔔 *SUBSCRIBE for weekly payroll growth strategies:* → Hit the bell to never miss an episode 💬 *CONNECT WITH MATT:* LinkedIn: https://www.linkedin.com/in/mattvaadi Facebook Group: https://www.facebook.com/groups/payrollinnovation 👉 *TODAY'S GUEST:* → Chris Clark, Marketing Coach at Underdog Sports → Chris Clark is the Marketing Coach of Underdog Digital, helping sports brands and growing businesses scale through content and AI-driven systems. With 15+ years in sports media and marketing, Chris now focuses on building practical AI workflows that drive real revenue. how to build an AI app how to build your own CRM how to build custom software how to build a sales automation system how to build a lead generation system how to automate sales with AI how to create business software without coding how to build software without developers how to use AI for business how to build AI tools for business what is vibe coding
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    52 min
  • Vensure Made 100 Acquisitions (Here’s Why It Actually Worked)

    Vensure Made 100 Acquisitions (Here’s Why It Actually Worked)
    Jan 8 2026
    📧 Get weekly payroll bureau growth strategies (1,000+ leaders subscribed): → https://www.payrollinpodcast.com/#subscribe Learn the explosive growth secrets behind Vensure’s 100 acquisitions and $30B in revenue in just 5 years. In this episode, Matt dives into how Vensure scaled their business to $30B by acquiring 100 companies over the past few years. He breaks down the key strategy behind their explosive growth and what this means for the payroll, PEO, and HR industries. Whether you're in payroll, HR, or running a business of any size, you’ll walk away with actionable insights on how to leverage acquisitions, tech, and niche markets to accelerate your own growth. From mastering acquisitions to navigating chaos at scale, this episode will give you a roadmap for making strategic moves in your own business. Don’t miss this industry deep dive! ⏰ *TIMESTAMPS:* 0:00 - Introduction 1:02 - The CEO’s Vision: The Strategy Vensure Laid Out 3:20 - Vensure’s Unique Approach to Acquisitions 5:22 - The Growth Curve: From 50,000 to 900,000 Employees 8:00 - Why Tech Ownership Matters in Vensure’s Model 10:00 - Practical Insights to Scale Your Payroll Business 12:20 - The Importance of Niche Markets and Recession Resilience 14:05 - How Vensure’s Strategy Creates High-Value Acquisitions 16:00 - Scaling Through Chaos: What It Means for Your Business 18:00 - Vensure’s Future and What It Means for the Payroll Industry 20:00 - Key Takeaways: Strategic Moves for Your Payroll Bureau 22:00 - Conclusion and Final Thoughts 📧 *GET THE INSIDER NEWSLETTER* Weekly strategies for scaling your payroll bureau (1,000+ bureau owners subscribed) → https://www.payrollinpodcast.com/ 🎯 *THIS WEEK'S RESOURCE:* Three Keys to Expand Your Payroll Business. Learn the top tactics to scale and grow your payroll company → https://youtu.be/6aW8RmVj8OE 💡 *SCALE YOUR BUREAU WITH OUR HELP:* 1️⃣ *Add PEO Services* - New revenue stream without new clients → Learn more: https://www.guhroo.co/partners/ 2️⃣ *Hire Virtual Assistants* - Scale operations at 70% less cost → https://www.outsourcedscale.com/ 3️⃣ *Marketing That Works* - Get the system we use → https://underdogdigital.co/ 🔔 **SUBSCRIBE for weekly payroll growth strategies:** → Hit the bell to never miss an episode 💬 *CONNECT WITH MATT:* LinkedIn: https://www.linkedin.com/in/mattvaadi Facebook Group: https://www.facebook.com/groups/payrollinnovation #payroll #payrollservices #bureauowner How do payroll companies grow fast What is an acquisition strategy How to scale a payroll business What is the PEO acquisition modelHow to buy other companies to grow your businessWhy are acquisitions important for business growthHow do acquisitions affect business growth What are the benefits of acquiring companiesHow do payroll companies increase market share What is the best strategy for business growthHow does Vensure grow its business
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    27 min