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. 3d ago

    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.
  2. 4d ago

    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
  3. 5d ago

    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
  4. 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
  5. Aug 20

    Your Gross Margin Is Misreported and Misunderstood

    If you are still delivering work yourself, the gross margin on your screen is probably not telling you the truth. Daniel Welling ran an information technology services business for 12 years, took it to around £1m a year in recurring revenue with 200 customers and 15 to 20 staff, then sold it. He now runs The MSP Finance Team, doing management accounting and fractional finance direction for MSPs, which means he spends his days inside other people's books. In this one he gives the benchmarks straight. Best in class blended gross margin sits in the 40% bracket. Most MSPs are somewhere between the early 20s and the mid 30s. And the reason so many owners think they are doing better than that is the same every time: they never load their own delivery time into cost of sales, they pay themselves mostly in dividends, and dividends never touch the profit and loss statement at all. So the number says 90% and the owner thinks they are a genius. His words: it is a misreported, misunderstood number. The bit that stings is what hides underneath it. The real cost of delivery and account management, he says, is totally masked by the enthusiasm, the energy levels and the work ethic of the owner. The business looks profitable because someone is quietly working for free. He also does the arithmetic almost nobody does out loud. Once acquisition is properly delegated, so not the owner and not a referral from a mate in the pub, winning a client can cost £20,000 to £30,000. Put 10% of a £1m business into sales and marketing and that buys you four new clients a year, which is probably not the growth you had in mind. The back half is the expansion that went wrong. He took the business into California chasing follow-the-sun support, the acquisition he had agreed collapsed, he built it from scratch anyway, closed new business on his first trip, flew home thinking he had cracked it, and had already made the mistakes that killed it. Commercially it worked. Delivery is what broke. What we cover Starting an IT services business in 2002, before the term MSP existedWhy he left the operator seat and went into finance insteadThe three finance mistakes he sees most, starting with reporting on a cash basis instead of an accrual basisWhy one blended gross margin line hides everything that mattersLabour-loaded gross margin, and the dividend problem that makes UK owners misread their own businessHow the UK 40% benchmark compares with the US, where the numbers run higherWhat a new client actually costs to win, and what that does to a sales and marketing budgetTaking a UK MSP into America, and the difference between the commercial side working and delivery failingThe Master MSP model: delegated delivery, turning on cost only when you turn on revenueThe phases of ownership, from engineer to salesperson to leader to shareholderWhy he is taking the finance business into a US market he reckons is 10 times the sizeFind Daniel on LinkedIn. It is the only channel he names on the episode.

    Your Gross Margin Is Misreported and Misunderstood
  6. Jul 23

    Buying MSPs at 1-2x Profit While the Market Pays 5-8x

    Peter Moriarty built itGenius, a Google-first, cloud-only MSP, from a $20-an-hour teenage side hustle into Australia's number one Google partner for small business. His growth playbook breaks every MSP convention: he serves the under-20-seat clients nobody else wants, buys distressed competitors at 1-2x profit while the market pays 5-8x EBIT, gets 90% of new clients from YouTube organically, and keeps 95% of acquired customers with a "give love" onboarding philosophy. We also get into the AI bot that's already eating his help desk, the labor-arbitrage model behind his "AirAsia of IT" pricing, and why he thinks level-one support is disappearing. What we cover: - The origin story: charging $20/hour at 15 because McDonald's paid $7 - Going all-in on Google in 2011 and becoming Australia's #1 SMB partner - The accidental YouTube channel that now drives 90% of new business - The M&A playbook: 11+ acquisitions, bootstrapped, at 1-2x profit - Post-acquisition churn: the "give love" philosophy and the break-lease analogy - Serving under-20-seat clients profitably: the "MSP Lite" model - Albert, the in-house AI bot resolving tickets before humans see them - Why level-one support is disappearing, and what MSPs should do about it Chapters: 00:00 Cold open: the "give love" churn philosophy 00:33 Intro 01:12 Origin story: teenage IT hustle to founding itGenius 02:42 Picking a lane: going all-in on Google 04:17 Scaling through partnerships and speaking 07:46 How YouTube became the #1 growth channel 10:50 The M&A playbook: buying at 1-2x profit 16:00 Keeping churn low after an acquisition 21:25 Cracking small clients at scale: the MSP Lite model 27:40 Bots eating the help desk 32:48 Staying ahead of Google's own AI 34:20 Quickfire round 40:31 Where to find Peter Guest: Peter Moriarty itGenius: https://itgenius.com Contact: peter@itgenius.com (itGenius is actively looking to acquire Google Workspace MSPs) Play It Smart is where the smartest founders in managed IT, security, and AI show how they actually build. New episodes on YouTube and every podcast platform.

    Buying MSPs at 1-2x Profit While the Market Pays 5-8x

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.