Play It Smart

Alexej Pikovsky

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.

  1. 2d ago

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

    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

    He Ran Security for The Weather Channel. Now He Keeps Factories and Fleets Online.
  2. 3d ago

    Why This Healthcare MSP Moved Every Client to One Security Standard

    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

    Why This Healthcare MSP Moved Every Client to One Security Standard
  3. Sep 11

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

    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

    He Sold His MSP to Private Equity. In 18 Months, Most Clients Left.
  4. Aug 31

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

    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

    Six Private Equity Offers a Week, and He Sold to His Staff Instead
  5. Aug 26

    He Ran IT Inside the Agencies. Then He Started Serving Them.

    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 month Georg Dauterman: https://www.linkedin.com/in/georg-dauterman/Valiant Technology: https://thevaliantway.comThe Creative Stack podcast: https://podcast.thevaliantway.com

    He Ran IT Inside the Agencies. Then He Started Serving Them.
  6. Aug 25

    The MSP Built for Clients Nobody Can Standardise

    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 leave Noah Landow: https://noahlandow.comMacktez: https://macktez.com

    The MSP Built for Clients Nobody Can Standardise
  7. Aug 24

    The $500K Wire That Turns an MSP Into the Defendant

    A client wires half a million dollars to a criminal. Their cyber policy covers a hundred thousand, maybe two hundred fifty. The plaintiff's attorney does the math and knows exactly who to go after next: the managed service provider (MSP). Joe Brunsman has watched this from every side. He runs the Brunsman Advisory Group, an insurance brokerage in Annapolis built around MSPs, spent fifteen years with the United States (US) Navy, holds a master's in cybersecurity law, and has dealt with close to a thousand cyber claims. His starting point: before 2020, lawsuits against MSPs effectively did not exist. He went looking and found two, one of them an employment claim. Then the plaintiff's bar noticed an industry with no licensing regime, no statutory protections, and clients who lose real money when something breaks. Breach litigation has gone parabolic since, and MSPs are being named as co-defendants. The myth he wants dead is claim denial. In 11 years he has never had a cyber claim denied, across close to a thousand claims. Cyber insurance is dirt cheap, the policies are broader than most people fathom, and they pay. What actually sinks MSPs is everything around the policy: an indemnification clause pointing the wrong way, a client who skipped their own cyber policy and plans to sue you instead, a definition of technology services narrower than what you actually do. So the episode builds his defense in depth for the business itself: the master services agreement (MSA) first, hold harmless and indemnification done right, contractually requiring clients to carry their own cyber insurance, then your own technology errors and omissions (tech E&O) policy on top. Plus the phrase that matters when artificial intelligence (AI) shows up in a claim: "including but not limited to." And his mutual insurance framing, which turns the client risk conversation into a reason to trust you. What we cover: Why MSP lawsuits barely existed before 2020, and what changed How a plaintiff's attorney builds a case against an MSP, played out through a half million dollar wire fraud The 2019 research that said you needed a billion dollar company and 200,000 lost records to get sued, and why it no longer holds Whether your client's cyber policy protects you (it protects them) Hold harmless and indemnification, one way versus two way Defense in depth applied to the business, not the network The claim denial myth: 11 years, close to a thousand claims, zero denied Subrogation, explained with a car crash The big client versus small client risk math Tech E&O decoded: the four buckets and the one definition to read Contra proferentem, the rule from the year 462 buried in every argument about vague policy language What happens when the claim involves AI, a rogue large language model (LLM), or an outsourced security operations center (SOC) that missed the alert How many MSPs actually carry tech E&O (his estimate: under half) Where liability lands next, and clients running AI over your MSA The mutual insurance framing that wins the client conversation Find Joe on YouTube (Joseph Brunsman), where everything is free and nothing is monetized, on LinkedIn, or at thebrunsgroup.com. His books include Damage Control: Cyber Insurance and Compliance.

    The $500K Wire That Turns an MSP Into the Defendant
  8. Aug 21

    Why a Three Person Fund Gets Billed for Ten Seats

    Most managed service providers (MSPs) price per seat and then quietly lose money on their smallest clients. Raffi Jamgotchian bills a three person firm for ten. He founded Triada Networks in 2008 and spent the early years taking whatever walked through the door. Four years in he looked back and noticed that of his first five or six clients, four or five were investment firms. He has aimed the business at financial services ever since. Not exclusively, he is clear he is no purist and plenty of those early non-finance clients are still with him, but that is who Triada markets to and who the business is built around. The pricing rule is the part worth stealing. Triada sets a floor at ten people. A three person fund pays the ten seat bill and keeps paying it until it grows into the number. That sounds aggressive until he explains it: the compliance layer takes roughly the same work whether the firm has three people, ten or thirty. Same labour, smaller invoice, so the money has to come from somewhere. He is careful about the reason, too. Plenty of these firms do grow, three people to seven in a couple of months, ten by the next year, maybe twenty after that. But he says the floor is not a bet on growth. Some clients decide to stay small and nimble and that is fine. The floor exists because there is a built in cost to servicing any regulated firm, whatever its size. Then there is the marketing, which nobody in his corner of the industry does. He runs Facebook and Instagram ads, and Instagram works best. His reasoning is simply that finance IT companies do not advertise, so turning up in the feed of someone who fits the profile is a pattern interrupt. People reach out. The ads point at a due diligence checklist he built from his last book. He is also blunt about where the industry is kidding itself. Asked what is most overrated right now, he says artificial intelligence (AI), and that everyone is sprinkling AI dust on places that do not need it. Asked what is most underrated, he says identity protection, human and non-human both. His own clients generated more support tickets once AI tools arrived, not fewer. When he asked other MSPs in his peer group, they were not seeing the same thing. What we cover How Triada ended up focused on financial services, and the four year delay before he noticedThe two client types today, alternative asset managers and independent wealth advisorsWhy teams breaking away from Charles Schwab, Merrill Lynch and UBS suddenly need an outside partnerWhat an investment firm needs that a manufacturer does notWhy investors started asking cyber due diligence questions before the regulator didSecurity in three places, identity, data and devices, and why the program beats the toolsWhere new clients come from, new funds versus firms leaving a generalist providerThe ten seat pricing floor, and why compliance work does not scale with headcountThe channel mix: referrals, chief compliance officers, commercial real estate brokers, ads and cold callingWhy Instagram ads work for an MSP selling to investment firmsSelling one all-inclusive tier instead of three, plus co-managed and advisory arrangementsWhen a firm should hire internal information technology (IT) staff instead of an MSPWhat AI actually did to his ticket volume, and the guardrails they builtThe move toward consumption based pricingThe lightning round: one tool he cannot work without, most overrated, most underrated, cloud or on-premiseFind Raffi on LinkedIn, where he says he posts videos regularly. He does not name a website or a book title on the episode.

    Why a Three Person Fund Gets Billed for Ten Seats

About

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.