The $27m MSP Playbook for Scaling Past $10M w/ Willis Cantey

The $27m MSP Playbook for Scaling Past $10M w/ Willis Cantey

Can your MSP scale without you? Take the free MSP Maturity Assessment. brianhoppe.com/assessment The people who help you get to one stage of growth are not always the people who can help you scale to the next one. As MSPs grow, the business changes. The owner can’t be the hero. The best tech can’t be the only person clients call. And the team cannot keep relying on individual effort instead of process, structure, and leadership. Brian Hoppe sits down with Willis Cantey, founder of Cantey Tech, to unpack how he grew a two-person IT support company into a roughly $27 million MSP with around 120 employees. This conversation gets into the real work of scaling an MSP, from getting out into the community and building trust, to hiring salespeople, investing in management before the payoff shows up, and moving away from the “Superman cape” model that keeps small MSPs stuck. Willis also shares what he has learned through acquisitions, organic growth, leadership development, vertical focus, private equity, and the hard people decisions that come with building a more mature company. In this episode: - Why MSP owners need to get out from behind the desk to grow - How Cantey Tech scaled through relationships, sales, and referrals - Why investing in management can shrink margins before it improves the business - How to move beyond the “hero tech” model and build a process-driven company - Why holding onto the wrong people too long can cost clients, culture, and growth - What Willis learned from acquisitions, integration, and protecting culture - How to develop leaders without forcing great techs into management roles If you’re an MSP owner trying to grow beyond founder-led chaos, build a stronger leadership team, and create a company that can scale without depending on superheroes, this is the conversation. Key Moments 0:00 - Introduction 1:07 - Meet Willis Cantey 1:29 - Growing from $5M to $10M 3:23 - Buying and building Cantey Tech 8:33 - Scaling to $27M and 120 employees 11:25 - Investing in management before the payoff 19:42 - Moving beyond the “Superman cape” model 24:22 - The cost of holding onto the wrong people 27:30 - Decisions that created disproportionate growth 30:39 - Vertical focus, markets, and specialization 39:43 - Acquisitions, culture, and integration 45:14 - Organic growth and sales strategy 48:01 - Developing leaders inside the company 58:03 - The role of the CEO at scale 1:01:52 - Willis’ biggest leadership mistake 1:03:31 - Rapid-fire questions and closing thoughts 1:06:16 - Where to connect with Willis Connect Brian Hoppe: https://brianhoppe.com/ https://www.linkedin.com/in/brianhoppe/ Willis Cantey: https://canteytech.com/ https://www.linkedin.com/in/williscantey/

Running an MSP Isn’t That Hard w/ Jesse Miller

Download the framework I use with $10M–$100M MSP owners: https://brianhoppe.com/blueprint/ [https://brianhoppe.com/blueprint/] A cybersecurity practice that actually sells. Not because the stack is better, but because the client finally understands the risk. Most MSPs know they need to mature their security offering. The harder part is getting clients to care, getting the team aligned, and turning cybersecurity into a strategic revenue engine instead of another set of tools. Brian Hoppe sits down with Jesse Miller, founder of Power PSA Consulting and creator of the Power Gryd vCISO system, to unpack what it really takes to build a cybersecurity practice inside an MSP. This conversation gets into the shift from selling controls to selling risk management, why paid assessments change the entire client conversation, and how strategic advisory can increase client lifetime value. Jesse also shares lessons from scaling an MSP from 5 people to 75, building a cyber program the hard way, navigating internal friction, and why vertical focus will matter even more as AI changes the industry. In this episode: * Why cybersecurity practices fail when MSPs lead with tools instead of risk * How paid risk assessments create better buyers and stronger relationships * Why vCSO and vCISO should be treated as real advisory services, not bundled extras * How to align sales, service, and leadership before launching a new practice * Why specialization, vertical focus, and strategic consulting are becoming harder to avoid If you’re an MSP owner trying to move beyond reactive IT, build stronger client relationships, and create a more valuable advisory-led business, this is the conversation. Key Moments 0:00 - Introduction 1:06 - Meet Jesse Miller 2:06 - Why MSP growth is simple, but not easy 4:09 - Jesse’s path from telecom to MSP cybersecurity 10:34 - Selling risk management instead of security tools 18:18 - Why every client needs a paid risk assessment 23:49 - Building true vCISO and vCSO advisory services 33:09 - Leadership lessons from launching a cyber practice 42:35 - Letting go, building smarter teams, and avoiding shiny object decisions 47:49 - AI, specialization, and the future of MSP strategy 56:00 - Jesse’s biggest leadership mistake 57:45 - Rapid-fire questions and closing thoughts 1:01:08 - Where to connect with Jesse Connect Brian Hoppe: https://brianhoppe.com/ [https://brianhoppe.com/] https://www.linkedin.com/in/brianhoppe/ Jesse Miller: https://www.linkedin.com/in/secopswarrior/ https://powerpsa.com/

What $100M MSPs Do Differently w/ Steve Torres

Download the framework I use with $10M–$100M MSP owners: https://brianhoppe.com/blueprint/ [https://brianhoppe.com/blueprint/] A $100M operator’s view of what actually makes an MSP valuable. Most MSPs do not stall because they lack effort. They stall because brute force stops working. Brian Hoppe sits down with Steve Torres, President of CFO for IT, to unpack the operational disciplines that separate MSPs that scale from the ones that stay trapped in founder-led chaos. Steve has helped scale multiple IT services companies beyond $100M, worked through roughly 20 acquisitions, and now helps MSPs build the financial and operational maturity needed to increase enterprise value. This conversation is not about tools, tactics, or chasing growth for growth’s sake. It’s about the systems, discipline, metrics, and decision-making habits that create a more valuable business. In this episode: * Why “brute force execution” quietly destroys enterprise value * The 6 disciplines Steve sees in MSPs that scale past $100M * Why strategy frameworks create clarity, alignment, and accountability * The metrics MSP owners should actually care about * How CRM discipline exposes the real bottlenecks in sales and marketing * Why standardized offerings improve margins, sales cycles, and delivery * How budgeting and rolling forecasts create better decisions * The leadership danger of hiring purely for intelligence If you’re trying to build an MSP that can scale without breaking, this is the conversation. Key Moments 0:00 - Welcome to The $10 Million MSP Podcast 1:07 - Brian introduces Steve Torres 1:41 - The blind spot hurting MSP enterprise value 6:22 - The 6 attributes of MSPs that scale past $100M 10:37 - Why strategy frameworks create clarity and alignment 15:13 - The metrics MSP owners should actually track 23:51 - Why CRM discipline is non-negotiable 28:06 - The cost of customized offerings 39:04 - Decisiveness, agile velocity, and failing forward 43:43 - Why budgeting discipline drives maturity 51:52 - Steve’s biggest leadership mistake 57:52 - Where to connect with Steve Connect Brian Hoppe: https://brianhoppe.com/ [https://brianhoppe.com/] Steve Torres https://www.linkedin.com/in/cfoforit/ https://cfoforit.com/

From $13M to $60M: What It Really Takes to Scale an MSP w/ Kevin Cook

A $13M MSP turned into a $60M platform in four years. That kind of growth does not happen because the founder works harder. It happens because the business becomes more valuable, less owner-dependent, and built for scale. Brian Hoppe sits down with Kevin Cook, Chief Strategy Officer at Ntiva and former CEO of The Purple Guys, to unpack what it really takes to move from founder-led MSP to private-equity-backed platform. This conversation gets into enterprise value, acquisitions, leadership development, AI, and the hard decisions owners face when they want the business to outgrow them. In this episode: * Why owner dependence is one of the biggest value killers in an MSP * How Kevin went from a $13M MSP to a $60M platform through PE and acquisitions * What acquirers actually look for beyond EBITDA * Why culture fit can make or break an acquisition * How AI is changing the timing and strategy behind MSP exits If you’re thinking about how to build a business that can scale, sell, or survive beyond you, this is the conversation. If you want to go deeper on the levers behind growth and valuation, you can get the Value Creation Blueprint here: https://brianhoppe.com/blueprint/ Key Moments 0:00 - Welcome to The $10 Million MSP Podcast 1:07 - Kevin Cook joins the show 5:29 - Taking on private equity and becoming The Purple Guys 13:36 - What creates enterprise value in an MSP 24:23 - How AI is changing the MSP landscape 32:22 - What changes after outside investment 37:20 - Why leadership development becomes critical 51:15 - Kevin’s biggest leadership mistake Connect Brian Hoppe: https://brianhoppe.com/ [https://brianhoppe.com/] Kevin Cook: https://www.linkedin.com/in/kevin-cook-ntiva/ https://www.ntiva.com/

How GCS Built A Durable $15M MSP w/ Shane Gronniger

A nearly $15M MSP in Austin. No acquisitions. No private equity. No traditional outbound sales machine. Most MSP growth stories focus on founder vision, aggressive sales, or rolling up other companies. This one is different. Brian Hoppe sits down with Shane Groniger, CEO of GCS Technologies, to unpack what it looks like to step into the CEO seat of a company he didn’t found and help move it past the $10M plateau. This is a conversation about discipline, focus, leadership maturity, and building a durable business without blindly following the standard MSP playbook. In this episode: - What it takes to lead an MSP you didn’t found - How GCS moved from an $8M-$9M plateau to nearly $15M - Why discipline, focus, and “addition through subtraction” became key growth drivers - How fixed-fee security packaging changed the business model - Why margin by client and agreement matters more than top-line revenue - The hard leadership lessons that come with putting people in the right seats - How Shane thinks about AI, automation, and the next curve jump for MSPs If you’re thinking about what has to change inside the business before the next stage of growth can happen, this is the conversation. If you want to go deeper on the levers behind growth and valuation, you can get the Value Creation Blueprint here: https://brianhoppe.com/blueprint/ Key Moments 1:06 – Shane Groniger joins the show 1:41 – Leading a company he didn’t found 3:01 – GCS Technologies’ journey to nearly $15M 6:29 – Breaking through the $8M-$9M plateau 7:28 – Revenue per employee, margin discipline, and EBITDA 8:50 – Moving into packaged cybersecurity services 10:54 – GCS’ ideal client profile 13:05 – Founder identity vs. non-founder CEO identity 19:03 – What had to change to get past $10M 21:54 – Building a lean leadership team 24:09 – What breaks between $8M and $15M 26:48 – The hard lesson of right people, wrong seats 31:19 – Growth plans from $15M to $20M 38:51 – Building a durable asset instead of chasing an exit 41:45 – Borrowing from EOS, peer groups, and industry benchmarks 44:42 – The metrics Shane watches most closely 49:02 – Why account management and retention matter more at scale 50:52 – Shane’s biggest leadership mistake 55:15 – Delegating decisions, not just tasks 56:35 – Lightning round 59:39 – Books and ideas that shaped Shane’s leadership Connect Brian Hoppe https://brianhoppe.com/ https://www.linkedin.com/in/brianhoppe Shane Gronniger GCS Technologies https://www.gcstechnologies.com/ https://www.linkedin.com/in/shanegroniger/