Play It Smart

Alexej Pikovsky

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Entrepreneurship
Updated Weekly

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.

6d ago

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.
Jul 21

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.
Jul 11

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.
12/06/2024

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.
11/29/2024

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.
10/28/2024

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/randfishkinWebsite: https://sparktoro.com/ 🔔 Stay Updated: Turn on notifications to never miss our latest videos on growth tactics in SaaS, trends, and business insights.
07/31/2024

From Viral B2C AI Video templates to leading AI Video SaaS platform

In this podcast episode, we dive deep into Rizzle's innovative journey from a short-form video platform to a leading SaaS for AI-driven video creation. Discover how Rizzle prioritizes product features, manages challenges, and envisions the future of video editing. Hear personal insights on fundraising, team dynamics, and the entrepreneurial spirit from the co-founder with a rich tech background. Don't miss key lessons and an inspiring success story on navigating the tech industry and scaling a startup. 🔍Timestamps: 00:00 Introduction to Product Features and Prioritization 01:03 What is Rizzle? 03:21 The Journey of the Founders 05:13 Pivoting the Business Model 12:15 Current Focus and Market Positioning 16:34 Team Structure and Engineering Talent 22:49 Building Brand Awareness and Moving Away from Free Models 23:10 The Future of Video Editing with AI 25:46 Challenges in Fundraising and Market Competition 29:44 Lessons Learned from Fundraising Struggles 35:18 Splitting Roles and Responsibilities in a Startup 36:26 Critical Lessons for SaaS Founders 39:48 Quick Fire Questions and Closing Thoughts -- LINKS -- ► Show Notes: nuoptima.com/saas-podcast/rizzle-vidya-narayanan 🔗 Follow NUOPTIMA: LinkedIn: https://www.linkedin.com/in/alexej-pikovsky-9743701/Website: https://www.nuoptima.com 🔗 Follow Vidya: LinkedIn: https://www.linkedin.com/in/hellovidyaWebsite: https://rizzle.com/ 🔔 Stay Updated: Turn on notifications to never miss our latest videos on growth tactics in SaaS, trends, and business insights.
07/01/2024

How to be a Tech Disruptor in One of the Oldest Sports Industries of our Time

In this podcast episode we dive deep into Pegasus, a pioneering SaaS platform transforming the equestrian event management industry. Sam, the founder, takes us through the company's vision of becoming the global operating system for the equestrian economy. Learn about their unique journey from bootstrap beginnings to launching with potential, powered by a strong marketing strategy and deep industry insights. Discover the challenges and triumphs of developing such specialized software, their strategic approach to market entry, and how they plan to dominate this niche yet lucrative industry. Perfect for tech enthusiasts, aspiring founders, and anyone with a passion for SaaS and equestrian sports. 🔍Timestamps: 00:00 Introduction and Welcome 00:07 Overview of Pegasus and Its Vision 01:46 Event Management System Features 03:12 Marketplace and Future Plans 05:29 Founder's Journey into Equestrian Tech 05:48 Building the Business During COVID 08:23 Initial Challenges and Launch 11:51 Marketing Strategy and Brand Building 13:24 Podcasting as a Growth Tool 18:44 Personal Podcast Preferences 23:14 CrossFit and Business Insights 27:53 CrossFit's Unique Business Model 29:20 The Appeal of CrossFit Competitions 31:01 Marketing Strategies in Sports 33:05 Building Pegasus: A Journey of Trust and Relationships 36:06 Soft Launch and Customer Feedback 38:57 Challenges and Strategies in Scaling 43:06 The Role of Venture Capital 46:03 Lessons from a Founder Couple 52:41 Contact and Final Thoughts -- LINKS -- ► Show Notes: http://nuoptima.com/saas-podcast/pegasus-sam-baynes 🔗 Follow NUOPTIMA: LinkedIn: https://www.linkedin.com/in/alexej-pikovsky-9743701/Website: https://www.nuoptima.com 🔗 Follow Sam: LinkedIn: https://www.linkedin.com/in/sam-baynes-1b039013b/Website: https://www.thepegasus.app/ 🔔 Stay Updated: Turn on notifications to never miss our latest videos on growth tactics in SaaS, trends, and business insights.

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.

Creator

Alexej Pikovsky
Years Active

2024 - 2026
Episodes

30
Rating

Clean
Copyright

© 2026 Alexej Pikovsky
Show Website

Play It Smart