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Play It Smart

Play It Smart

Hosted by Alexej Pikovsky

Episodes

34

Latest episode

Aug 2026

Language

EN

About the show

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.

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34 recent
August 21, 2026Episode 743 min

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 noticed The two client types today, alternative asset managers and independent wealth advisors Why teams breaking away from Charles Schwab, Merrill Lynch and UBS suddenly need an outside partner What an investment firm needs that a manufacturer does not Why investors started asking cyber due diligence questions before the regulator did Security in three places, identity, data and devices, and why the program beats the tools Where new clients come from, new funds versus firms leaving a generalist provider The ten seat pricing floor, and why compliance work does not scale with headcount The channel mix: referrals, chief compliance officers, commercial real estate brokers, ads and cold calling Why Instagram ads work for an MSP selling to investment firms Selling one all-inclusive tier instead of three, plus co-managed and advisory arrangements When a firm should hire internal information technology (IT) staff instead of an MSP What AI actually did to his ticket volume, and the guardrails they built The move toward consumption based pricing The lightning round: one tool he cannot work without, most overrated, most underrated, cloud or on-premise Find Raffi on LinkedIn, where he says he posts videos regularly. He does not name a website or a book title on the episode.

August 20, 2026Episode 644 min

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 existed Why he left the operator seat and went into finance instead The three finance mistakes he sees most, starting with reporting on a cash basis instead of an accrual basis Why one blended gross margin line hides everything that matters Labour-loaded gross margin, and the dividend problem that makes UK owners misread their own business How the UK 40% benchmark compares with the US, where the numbers run higher What a new client actually costs to win, and what that does to a sales and marketing budget Taking a UK MSP into America, and the difference between the commercial side working and delivery failing The Master MSP model: delegated delivery, turning on cost only when you turn on revenue The phases of ownership, from engineer to salesperson to leader to shareholder Why he is taking the finance business into a US market he reckons is 10 times the size Find Daniel on LinkedIn. It is the only channel he names on the episode.

August 7, 2026Episode 537 min

Stop Selling to the Office Manager: How an MSP Owner Became the Board's vCISO

“It's the biggest risk to their business, almost certainly.” Dave Lane has run an MSP since 2006, moved it from the UK to Malaga, and then did what most MSP owners only talk about: he stopped competing in the break-fix race to the bottom and rebuilt the business as fractional IT leadership and vCISO work, sold directly to boards. We get into why he could not deliver real business value while his contact was the office manager, what shadow AI does to a company that thinks it has IT under control, and why good governance starts with people, not tools. What we cover: - Building an MSP from 2006 and moving it from the UK to Malaga - Why break-fix stopped being defensible and what he rebuilt instead - Selling direct to boards, and the “two bosses” problem of working through MSPs - Shadow IT vs shadow AI, and why the second one is worse - Governance without surveillance: policy, training and least privilege over spying (yes, the mouse jiggler story) - AI security tooling that cost tens of thousands of pounds a month five years ago and hundreds now - Why one- and two-person MSPs face a consolidation wave as cyber and AI risk outgrow them Connect with Dave: LinkedIn: https://www.linkedin.com/in/davelane/ Good Choice IT: https://goodchoiceit.co.uk Amalan Advisory (vCISO): https://advisory.amalan.co.uk

August 5, 2026Episode 434 min

You Can't Take AI to Court: Why Compliance Still Needs Humans

“You can't take AI to court. You have to take a person.” That one line is how Tim Golden thinks about compliance in the AI era. Tim ran a 100% federal-government MSP for 25 years with almost no tools, then turned the compliance work he kept giving away for free into Compliance Scorecard, a governance platform built for MSPs. We get into why the product costs $89 and stays that way, why he refuses to pay for ads, and what building a channel vendor actually looks like from the inside. What we cover: - 25 years running a federal MSP with almost no tools (while holding FedRAMP moderate) - Giving away two days a week for free until it had to become a product - Lead gen with zero paid ads: community, referrals, and showing up - “AI suggests, humans approve” and who answers when auditors come knocking - The $89 pricing bet and why he won't chase enterprise - CMMC in plain English: close to 50 MSPs walked through it, seven perfect 110s - What a raise actually buys: “poof, a million dollars goes quick” - Profitable and beating monthly goals every month since September Connect with Tim: LinkedIn: https://www.linkedin.com/in/timothygolden Compliance Scorecard: https://compliancescorecard.com/ Tim's podcast: https://mspthoughtleadership.com/

July 23, 2026Episode 340 min

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.

July 21, 2026Episode 235 min

The Google-Only MSP That Turned Its Audit Into a SaaS

Dan Taylor built one of the most unusual MSPs in the world. It's Google-only, it serves international schools only, and it runs on a small remote team spread across five countries. No Microsoft, no local market, no office. Then he turned his own Google Workspace audit into a product other MSPs buy, and it took off almost immediately. We get into how he went from Deloitte to a failed recruitment agency and then stumbled into the Google-for-education world, why niching down twice made the business instead of limiting it, how Google quietly took the schools market from Microsoft with almost no salespeople, and what it really takes to turn a service into a product. What we cover: - Why "Google-only, schools-only" was the whole advantage - Running a seven-figure MSP on almost no external software - The jump from $6k manual audits to a real SaaS product - Whether AI and "vibe coding" threaten a niche tool like his - His honest take on where MSPs should niche to actually make money Chapters: 00:00 Intro 00:35 From Deloitte to a failed recruitment agency 02:26 The random tip that started a Google empire 06:49 Why international schools became the niche 10:17 How Google beat Microsoft with zero salespeople 12:41 Running a remote MSP across five countries 15:48 From $6k manual audits to WorkspaceAudit 23:22 Can vibe-coding kill his SaaS? 32:30 Lightning round 34:56 Where to find Dan Guest: Dan Taylor AppsEDU: https://appsedu.com WorkspaceAudit: https://workspaceaudit.com Dan on LinkedIn: https://www.linkedin.com/in/appsevents/ Play It Smart is where I sit down with the founders and operators building in managed IT, security, and AI. New episodes on YouTube and every podcast platform.

July 11, 2026Episode 137 min

140 Clients, No Employees: How a Solo MSP Does It

Marco Hernandez runs a one-man MSP with 140 clients, gets 100% of his leads from referrals, and closes every deal he quotes. This episode takes apart exactly how. Marco was on his way to becoming a lawyer in Venezuela when a computer repair shop tried to screw him. Thirty years later he runs TEK IT UP IT Services, a deliberately solo MSP in the Greater Toronto Area, and he has turned being small into his biggest advantage. What we cover: 00:00 Cold open 00:21 Intro 01:12 Origin story: from law student to IT 02:47 Going solo on purpose 05:51 Winning clients with 100% referrals 18:52 Pricing and scope creep 23:36 AI in a one-man MSP 33:46 Rapid fire round 36:39 Closing Play It Smart is the show where Alexej Pikovsky sits down with MSP operators and takes apart how they do it.

December 6, 2024Episode 2946 min

Turn Clicks Into Cash: Conversion Hacks Every Business Needs

Oliver Kenyon is a UK-based entrepreneur and the Co-Founder of ConversionWise, a company specializing in conversion rate optimization (CRO). Under his leadership, ConversionWise has collaborated with over 3,500 brands, including GFUEL, Lotus Biscuits, and Lamborghini, as well as prominent figures like Lionel Messi and Kim Kardashian. He is also the Founder of AffiliateFix, a leading affiliate marketing community that grew to over 70,000 members and 400,000 discussions. This platform was later acquired by Neil Patel’s investment firm in 2017. Before his entrepreneurial ventures, Oliver was a fully qualified chef. Beyond his business achievements, he is dedicated to education, offering courses on platforms like Udemy to share his expertise in CRO. Summary In this episode with Oliver Kenyon, you’ll learn: How Oliver built ConversionWise, a large conversion rate optimization (CRO) agency, including how they helped put landing pages on the map. Since the landing page industry exploded, how ConversionWise has evolved and adapted. When Oliver met his co-founder Andy and how they divide their workload. Whether they have any systems in place, such as EOS (Entrepreneurial Operating System) or OKR (Objectives and Key Results). The current status of the affiliate community that Oliver built (and his first exit), AffiliateFix. Whether Oliver started out specifically aiming at eCommerce or if he had adopted a more general approach. Some examples from Oliver of best practices that apply across the whole industry. Where Oliver sees issues where direct response does not really work but conversion is optimized, such as traffic that is too expensive. Whether Oliver thinks tech stack and brand infrastructure can affect conversion. How he feels about the future, including CMS (content management systems), Shopify, and AI. How ConversionWise works with brands on the CRO side and what their retention is like. How you can get in touch with Oliver.

November 29, 2024Episode 2734 min

Don’t Dilute Your Ownership! The Debt vs Equity Debate Every Tech Founder Needs to Hear

In this episode with Luc Arama, you’ll learn: HSBC Innovation Banking’s acquisition of Silicon Valley Bank (SVB) and Luc’s feelings about it. How companies manage a debt facility with SVB in both the UK and the US. Why a founder should consider going down the debt route rather than the equity route. At what stages does HSBC Innovation Banking lend to companies. What terms HSBC Innovation Banking usually offer for someone who is raising money through both an equity round and a venture debt facility. How HSBC Innovation Banking differentiates itself in the market against traditional banks, venture debt funds, and VC funds. How it differentiates from revenue-based financing. Why HSBC Innovation Banking helps so many software companies compared to e-commerce. What the due diligence process is for HSBC Innovation Banking when it underwrites. Examples of covenants being breached and what happens if they are breached. What needs to happen for HSBC Innovation Banking to auction off a business. How Luc sees the financing landscape evolving in the future. How you can get in touch with Luc.

October 28, 2024Episode 2557 min

The Path to Independent Success: Rand Fishkin on How to Build Without VC Funding

In this podcast episode, Alexej and Rand Fishkin discuss the advantages of angel funding over venture capital for startups, emphasizing sustainable business growth over rapid scaling. Rand shares insights from his experience with Moz and SparkToro, highlighting alternative investment structures and the potential impact of AI on search and SaaS industries. They also explore wealth-building approaches for entrepreneurs and the importance of antitrust policies in fostering innovation. 🔍Timestamps: 00:01 Alexej welcomes Rand to the conversation 00:44 Rand introduces himself, discussing Moz and SparkToro 02:19 Discussion on non-VC funding choices 04:40 Reasons for preferring angel investment over VC 08:34 Critique of the venture capital model 13:57 Explanation of SparkToro’s unique funding terms 18:19 Approach to building profitable, sustainable businesses 22:18 Liquidation preferences and SparkToro’s terms 24:31 Structure of SparkToro’s board and decision-making 29:27 Investors overlapping in multiple projects 34:01 Future of search and AI's impact on Google 38:03 Discussion on AI's role in SaaS 42:05 Implications of AGI and SaaS models 45:07 Wealth-building through sustainable entrepreneurship 51:54 Challenges of modern entrepreneurship and monopolies 57:00 How to connect with Rand on LinkedIn and Threads -- LINKS -- ► Show Notes: https://nuoptima.com/saas-podcast/sparktoro-rand-fishkin 🔗 Follow NUOPTIMA: LinkedIn: https://www.linkedin.com/in/alexej-pikovsky-9743701/ Website: https://www.nuoptima.com 🔗 Follow Rand: LinkedIn: https://www.linkedin.com/in/randfishkin Website: https://sparktoro.com/ 🔔 Stay Updated: Turn on notifications to never miss our latest videos on growth tactics in SaaS, trends, and business insights.

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