Play It Smart

By 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... more

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FAQs about Play It Smart:

How many episodes does Play It Smart have?

The podcast currently has 33 episodes available.

Play It Smart episodes:

August 07, 2026 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
...more
39min
August 05, 2026 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/
...more
35min
August 05, 2026 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/
...more
35min
July 23, 2026 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: [email protected] (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.
...more
41min
July 21, 2026 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.
...more
36min
July 11, 2026 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.
...more
38min
December 06, 2024Turn 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.
...more
46min
November 29, 2024Don’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.
...more
35min
October 28, 2024The 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.
...more
58min
July 31, 2024From 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/hellovidya
Website: https://rizzle.com/
🔔 Stay Updated: Turn on notifications to never miss our latest videos on growth tactics in SaaS, trends, and business insights.
...more
48min

FAQs about Play It Smart:

How many episodes does Play It Smart have?

The podcast currently has 33 episodes available.