Play It Smart

Play It Smart is the show where Alexej Pikovsky sits down with MSP operators and business owners and takes apart how they actually do it: winning clients, pricing, staying lean, using AI, and building toward an exit worth having. Season 2 is dedicated to MSP operators. Past guests include Rand Fishkin of Moz and SparkToro and the founders of Chili Piper, Flowchat and 3DLOOK.

Play It Smart is a business podcast hosted by Unknown Host, with 41 episodes on record and a Required Pod Score of 80.

Unknown Host hosts Play It Smart, a business show with 41 episodes published.

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  Episode #15

  Your Difficult Client Might Just Be a Pipeline Problem

  Sep 25, 202636 min

  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/

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  Episode #14

  He Ran Security for The Weather Channel. Now He Keeps Factories and Fleets Online.

  Sep 17, 202637 min

  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

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  Episode #13

  Why This Healthcare MSP Moved Every Client to One Security Standard

  Sep 16, 202631 min

  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

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  Episode #12

  He Sold His MSP to Private Equity. In 18 Months, Most Clients Left.

  Sep 11, 202641 min

  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

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  Episode #11

  Six Private Equity Offers a Week, and He Sold to His Staff Instead

  Aug 31, 202639 min

  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

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