Play It Smart

“good sales organizations are effectively systems, right?” Dave Wilkeson Hiring a salesperson without a sales system leaves them trying to solve a problem the owner hasn't solved. Dave Wilkeson of MSP Advisor joins Alexej Pikovsky to explain what needs to be in place first, and how managed service provider (MSP) owners can build a more profitable business as client expectations change. What we cover: - Why referrals become harder to rely on as an MSP grows.- How to develop sales capability around the owner before handing it over.- Why true net profit can differ from the number on your profit and loss statement.- Dave's 62% labor-loaded gross margin target and the tradeoffs between labor and tools.- The case for bundling Microsoft licensing, plus the contract risk it creates.- How account managers and structured client meetings support retention and expansion.- Why artificial intelligence (AI) services and consolidation are putting new pressure on smaller MSPs. Connect with Dave: - MSP Advisor: mspadvisor.com- Instrumental: instrumentalmsp.com Chapters 00:00 Why a salesperson needs a sales system00:41 Meet Dave Wilkeson02:25 Measuring real profitability06:47 Labor, automation and pricing14:29 Bundling Microsoft licensing18:39 Building a sales system25:08 Account management and retention29:52 AI and the client relationship36:07 Consolidation and smaller MSPs39:59 Lightning round and contact details

"Every single client that was a client came from Sachin. So we got to $20 million just on his back." Bryan Lukralle, chief strategy officer at Charter Technology Solutions (CTS), explains how the managed service provider (MSP) built its business around schools and nonprofits, then found new ways to bring in clients. He says the company reached $20 million with founder Sachin Gujral driving sales. Today client managers, specialist salespeople and website leads all add to that. Bryan joins Alexej Pikovsky to talk about serving clients with fixed budgets, growing beyond a local niche and keeping the company independent. He also shares what changed his mind about artificial intelligence (AI) assisted coding, the internal tools his team now uses, and the questions CTS still needs to answer before selling custom AI development to clients. What we cover: - What a chief strategy officer actually does inside an MSP - Building cyber advisory services around school budgets - How E-Rate funding affects project demand and the revenue mix - Why a strong school niche does not make geographic expansion easy - Splitting responsibilities between the founder and delivery leadership - Adding client referrals, specialist salespeople and website leads to founder-led sales - Keeping CTS independent while leaving future acquisitions open - AI governance, internal tools and the unresolved economics of client development work - Supporting Google, Microsoft, Macs and Windows, and the changing path into an IT career Bryan Lukralle: https://www.linkedin.com/in/bryanlukralle/ Charter Technology Solutions: https://charterts.com/

Buying a managed service provider (MSP) is only the start. Earl Foote, founder and chief executive of Nexus IT, has done 12 deals, eight in Utah and four outside it, and he explains how his team brings each acquired business into one brand, one operating model and a shared technology stack. Earl joins Alexej Pikovsky to talk about the capital search behind Nexus's acquisition strategy, the people and systems it takes to integrate a deal, and why a collection of separate businesses can be harder to sell. He also shares where artificial intelligence (AI) is already doing useful work inside Nexus, including service desk and escalation workflows he says save roughly 400 staff hours a month. What we cover: - Moving from opportunistic acquisitions to a defined buying strategy - Finding capital while keeping founder control - How Nexus assesses acquisition fit, margins and cash flow - The work behind combining teams, systems and brands - Keeping local client relationships as the platform grows - AI in dispatch, service desk and security operations - Where smaller MSPs have an early edge in bespoke AI services, and why Earl still expects scaled platforms to win Earl Foote: https://www.linkedin.com/in/earlfoote/ Nexus IT: https://www.nexusitc.net/

A managed service provider (MSP) owner stood up at an industry event and complained about an aggressive, demanding prospect. Tarek Meliti suggested the issue might not be the prospect at all, but a lack of opportunities in the pipeline. Tarek has run TDM Group, an MSP based in London, since 1997, mostly serving investment banks, hedge funds and other financial services clients. After roughly a decade of informally supporting UK clients' offices in the Middle East, TDM made regional expansion an explicit strategy about a year and a half ago, opening in Saudi Arabia, Qatar, the Emirates and Kuwait. In this episode of Play It Smart, Alexej Pikovsky talks with Tarek about competing on value instead of price in a crowded market, starting a business straight out of university before he had enough experience, and running an internal "AI month" that gave every employee a budget to experiment with artificial intelligence (AI). They also get into locking down AI agent permissions, what Broadcom's price increases on VMware taught him about vendor lock-in, and his advice for someone starting an MSP solo. What we cover: - Why TDM made Middle East expansion an explicit strategy after a decade of informally following UK clients there - Competing on value instead of price when entering the Emirates, and staying selective about which clients to take on - Targeting Dubai International Financial Centre (DIFC) clients through certifications and an existing network - Starting TDM Group right out of university with two friends, and the advice he'd give his own son about doing it too soon - Running an MSP across Ireland, the UK, America, Jordan and a Dubai back office, and hiring for values over skills - The industry-event story where Tarek reframed a difficult prospect as a possible pipeline problem - Searching for the right peer group after hearing, with caveats, that many MSPs stay under $1 million in revenue - Getting more from Microsoft 365 licenses clients already own instead of selling them another tool - An "AI month" with no budget limits, and why he calls AI adoption non-optional - Locking down AI agent permissions so client-built agents don't get admin-level access they shouldn't have - Why he says using AI to write conventional software beats running AI to operate it, on cost - Why Tarek sees Broadcom's price increases on VMware as a warning about getting stuck with one vendor, and building with containers and Kubernetes instead - Lightning round: the one tool he can't run TDM without, and why he thinks human skills, not technology, are most underrated - Cloud versus on-premises in five years, and running TDM's own data centers for clients who can't move to the public cloud - His advice for someone starting a solo MSP tomorrow: specialize on one cloud product and don't chase every client Tarek Meliti: https://www.linkedin.com/in/tarek-meliti/ TDM Group: https://www.tdmgroup.net/

If a just-in-time supplier is late with a windshield, the entire car plant shuts down, and John Penrod says that supplier can be fined $50,000 every 15 minutes. Customers like that have to stay up. At Transcend Networks, his managed service provider (MSP), that means redundancy and monitoring built so something can fail while operations keep running, plus recovery plans that start from what the business needs. Then the same lessons go to their smaller clients. John founded Transcend Networks, an Atlanta MSP, in 2003. He ran it solo for a number of years and brought on a partner in 2014, and today they own it 50-50: John's background is technology and information security, his partner's is operations and sales. John has also served as chief information security officer (CISO) at the Weather Channel. Automotive manufacturing is one of the firm's best core businesses. Word of mouth brought in broadcast video and state government work, and the best fit right now is companies with 25 to 75 users. What we cover: - How a late windshield can shut down an entire car plant, and the fine he says the supplier faces - Redundancy and monitoring, so something can fail while operations keep running - Why a disaster recovery plan starts with business needs, and what an outage would mean for a client with one server - A Kaseya and Datto shop that adds open-source tools such as Zabbix where they are needed - Cold calling, a full-time vice president of sales, and speaking at the Georgia Automotive Manufacturers Association - Using artificial intelligence (AI) for engineering answers that once took days with a vendor, while keeping confidential data out of it - Buyers who call about acquiring the firm, and why he treats every one of those calls as training - Phishing emails that include an entire conversation thread, so the request looks already approved - The good hurricane: a speaking engagement from his Weather Channel days, and why more business from fraud is still a shame - Scam Microsoft Teams calls, money wired abroad that you will never see again, and the time Hong Kong police laughed at him - Cyber insurance checklists that can be almost impossible to satisfy, and why you still have to have it - Open source where necessary, rather than where possible - Getting a busy client's time for the risks, from admin rights to bad batteries - Co-managed information technology (IT): a client's own IT person takes tier one and Transcend covers tier three and higher - Letting clients hear they are down from their provider before the front desk tells them - Staff on site full-time at state agencies in Georgia and North Carolina, working at the client's pleasure - After a larger equity-backed MSP bought the firm he worked at, the sales meeting where losing five customers and gaining 10 counted as a net win - Lightning round: deep web monitoring as a scare tactic, and training with simulated phishing as the most underrated thing - Cloud or on-premises in five years: VMware licensing, Azure costs and a dishwasher that has to be online for rinse mode - The MSPs that survive the next five years, and starting out on open-source tools John Penrod: https://www.linkedin.com/in/penrodcc Transcend Networks: https://www.tnius.com

Stuart Millington runs Bluebird IT, a healthcare-focused managed service provider (MSP) in Mandurah, Western Australia. Bluebird started with three pricing tiers, went down to two, and ended with one set of security standards that every client follows. When he told clients "this is our price, this is what it is," the ones who came back to him simply said: okay, I understand. About 85% of his clients are in healthcare, and the person Bluebird works with day to day is the practice manager, who takes pressure from doctors, owners, receptionists and patients. Stuart explains how his team takes vendor problems off their plate, how a traineeship in Broken Hill led to an MSP of his own, and the accountability group where things took off. He also shares why clients now tell him they found Bluebird on ChatGPT and Claude, and why his long-term goal is a business one of his children can take over. What we cover: - Moving from three pricing tiers to one security standard every client follows - When healthcare became the rule, and the finance, recruitment and arborist clients who stayed - Pointing prospects outside healthcare to other providers he trusts - Starting with general practices and aged care, then serving the wider medical industry - Why the practice manager is the linchpin, and dealing with their software vendors for them - Turning workflows and automation into monthly recurring revenue, this quarter's goal - From a one-year traineeship in Broken Hill to fixing cash machines in Perth - The boss who became one of his biggest role models in the industry - Starting Bluebird IT, then joining the Peel Chamber and Tech Tribe early on - An accountability group of six MSPs in different states - Sharing a building with a National Disability Insurance Scheme (NDIS) organization that Bluebird supports - Pushing through a hard first year and a half - Referrals, local networking, and the answer engine optimization (AEO) and generative engine optimization (GEO) work on his website - Where practice managers spend time online: Facebook groups over LinkedIn - Why he would rather help than sell: helping the people who fix the people - The stack: HaloPSA, NinjaOne, Huntress and Hudu, plus site photos for clients 20 hours apart - Australia's Privacy Act, keeping data in the country, and DefensX for controlling artificial intelligence (AI) access - Keeping the pull of shiny new tools in check with peer accountability - Best Practice and MedicalDirector building AI into clinical software - Monthly reports in HaloPSA as proof for Royal Australian College of General Practitioners (RACGP) audits - American buyers moving into the Australian MSP market - A long-term goal of handing the business to one of his children - Systems solid enough for probably another 300 devices before the next hire - Lightning round: Hudu, AI hype and hardware prices, client relationships, cloud, and MSPs that help each other grow Stuart Millington: https://www.linkedin.com/in/stuartmillingtonmandurah Bluebird IT: https://bluebirdit.com.au

Shawn Walsh built his managed service provider (MSP) in the basement of his house, grew it to locations in four states with six acquisitions, and sold it to private equity. Within 18 months the buyer had lost most of the clients and almost all of the employees. His diagnosis takes one sentence: they thought they had bought a technology company, and what they had actually bought was a relationship company. Before the MSP, Shawn ran a detective division and taught computer forensics at the New Hampshire Police Academy, until the consulting he did on his days off paid more than the day job. Now he coaches MSP owners at Encore Strategic, and this episode is his playbook: hire for character and teach the skills, follow your own process every time, know your end game before you sell, and understand why a specialist commands a far higher price than a generalist when the business goes to market. What we cover: - What private equity gets wrong when it buys an MSP - The greatest lie when private equity acquires you: nothing is going to change - Quote turnaround going from 48 hours to over three weeks after the sale - Why the buyers who get it leave the leadership team in charge: if the recipe works, why change it? - From head of a detective division to an MSP in the basement - Lawyers, medical practices and banks: clients with security and compliance obligations - Six acquisitions, four states, and an approach six years into a 10 year exit plan - Hiring for culture fit, personality profiling and emotional intelligence - Hungry, humble and smart, and why the technical skills can be taught - Why skipping his own hiring process cost him every single time - Peer groups, direct coaching and a deep dive on the finances - The first question he asks every owner: what is the end game? - Profit Grow Exit, his new book, and its first chapter, Begin with the End in Mind - A little rudder far from the rocks, a lesson from the Coast Guard - Assessing maturity as well as revenue - The owner demoted to a lower peer group who then doubled his company and tripled his profitability - Why specialists charge a premium and attract strategic buyers - A $12 million nanny payroll company that financial buyers valued at 10 to 12 million and a strategic buyer bought for $55 million - The Pumpkin Plan for Managed Service Providers, and a hedge-fund-only MSP that drew an 18X offer - Gross profit as the first number he checks, and why 55 to 65% is the healthy range - About half his MSPs already sell artificial intelligence (AI), and the smart ones build guard rails first - Consolidation, $100 million MSPs, and why he thinks lifestyle MSPs will disappear Shawn Walsh: https://www.linkedin.com/in/encorestrategic Encore Strategic: https://encorestrategic.io

Eric Rieger spent six years researching how to sell his managed service provider (MSP) to the people who worked in it, then about twenty minutes signing the paperwork. Private equity had been calling for years. Handwritten letters to his home address, his mobile ringing, six or seven offers in a week once WEBIT Services crossed $5 million in revenue. He turned all of it down, because the people who built the company had become his friends and he could not picture handing them a new owner on his way out the door. This is the exit conversation almost nobody in managed IT has on the record, with the numbers attached. About $70,000 to set the employee stock ownership plan (ESOP) up, and up to a quarter of a million for companies with a messier structure. Five or six thousand a year to administer, plus a $10,000 to $15,000 annual valuation. Four prerequisites before anyone should attempt it. A seller note instead of a bank, because he wanted to stay in control of the payments. And then the part nobody warns you about: how an employee actually turns those shares into money, and how you design the payout schedule so a wave of retirements cannot drain the business. Eric also explains why he thinks the door is closing. Private equity is lobbying Congress to make employee ownership harder, because it sees fewer than seven thousand employee-owned companies in America and still treats them as a threat. He is writing a book about all of it. What we cover: - Titanic Enterprises: a T-shirt side business, named as a joke about two fathers who were terrible at business - Talking his way into a software developer job without ever having written code - Quitting, then being hired back as a consultant, which became the first MSP contract before either of them knew the term - Four colleges, a materials management degree, and thirty years of fits and starts - Robin Robbins, Gary Pica and TruMethods as the education he never got in school - Letting go of operations early, because the tech never excited him and the sale always did - His four pillars: people, operations, finance, and sales and marketing - Small Giants, open book management, and 2016 as the year the direction changed - Referrals, the nonprofit niche, and the warm 250 after every outside marketing channel failed - Handwritten letters at home and six offers a week once revenue crossed $5 million - What an ESOP actually is: a trust, ERISA, shares issued every year, a valuation every year - What it costs, to set up and to run - The four prerequisites: $5 million in revenue, twenty employees, taxes paid, no debt - Why he started at 30%, and the seller note that made him the bank - An independent valuation that came back higher than he expected - Selling the other 70% by merging into an employee-owned holding company - Vesting cut from six years to three, and 4% 401(k) matching for his team - How an employee gets liquidity, and the payout design that protects the cash - The fractional chief financial officer (CFO) who pushed the merger through knowing it would end her own engagement - People over profits, and why he is not an anti-capitalist - Private equity lobbying Congress to make employee ownership harder Eric Rieger: https://www.linkedin.com/in/ericrieger WEBIT Services: https://webitservices.com

Georg Dauterman came to managed IT from the other side of the desk. A history degree, a quarter-life crisis, a Mac repair bench, then years running IT inside publishing houses and a Havas ad agency. In 2004 he quit, with a three-month-old at home, and joined Valiant Technology: a Mac-heavy managed service provider (MSP) for creative agencies in New York and Los Angeles, built when everyone else sold Windows and called it a day.We get into how a creative-only practice actually runs. Every engineer gets a Mac and Parallels and a 90-to-180-day onboarding. Freelancers work in isolated environments priced so agencies can grow and shrink. The buying moment is not a breach, it is the day an agency hires a chief operating officer (COO) who reads the master service agreement (MSA) and realizes there is no HR, no finance, no IT. And after a year of outbound experiments that did not yield, the pipeline runs on referrals, Google reviews, in-person networking and his own podcast.What we cover:- Running Valiant on the Entrepreneurial Operating System (EOS), with the integrator seat split across two people- Core values you can live with, and why "cheer" made the list- A history degree, a Mac repair bench, and an education inside a Havas agency- Quitting in 2004 with a newborn at home to join a non-cash-flowing business- Block hours and hands-on work before the remote monitoring and management (RMM) tool existed- The RMM-plus-cloud inflection that created the MSP industry, and why AI feels the same- A Service Leadership peer group as his master's degree in business- Cross-training every engineer, Mac and Windows both- The unmanaged Macs sitting in your clients' boardrooms- Due diligence questionnaires (DDQs), MSAs and the trust chain that makes agencies buy- Employees and freelancers as two separate user classes- Referrals, Google reviews and a podcast instead of a thousand dials- The quarterly committee that decides the product stack- Managed Model Context Protocol (MCP) servers for under $2,000 a monthGeorg Dauterman: https://www.linkedin.com/in/georg-dauterman/Valiant Technology: https://thevaliantway.comThe Creative Stack podcast: https://podcast.thevaliantway.com

Noah Landow co-founded Macktez in 1996 and is still running it, still independent, and still deliberately not built like the rest of the industry. Most managed service providers (MSPs) chase one stack across every client because that is what scales. Noah spent 25 years reluctant to use the label at all, because his clients cannot be standardised: nonprofits, cultural institutions, organizations in the middle of a build, and a public park in the middle of the Hudson River.We get into the mechanics. How he staffs jobs where the delivery date beats the supply chain. Why he keeps a closet of decommissioned switches and a cabling team on the payroll. What his recurring revenue number actually means once you strip out the five-year projects billed as subscriptions. And how a firm with no outside money reads the private equity money now moving through the channel.What we cover:- Taking jobs where the deadline cannot move, and phasing the network in anyway- Buying equipment six months early against a nonprofit's three-year budget- Keeping cabling in-house with almost no temporary staff- The 25 years he called it IT consulting instead of managed services- Co-managed work as a live negotiation over who does which step- What the 65 to 70 percent recurring figure hides- The three business units: managed services, consulting, physical installation- Where clients come from after 30 years, and the window in which a buyer is reachable- A two-year evaluation cycle before changing a ticketing system- Why JumpCloud changed the shape of the work- Thirty calls with private equity and venture groups, and what he makes of them- Single-vendor lock-in and what it costs to leaveNoah Landow: https://noahlandow.comMacktez: https://macktez.com