Play It Smart

By Alexej Pikovsky

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Category: Entrepreneurship

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Episodes: 30

Description

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.

Episode Date
Buying MSPs at 1-2x Profit While the Market Pays 5-8x
Jul 23, 2026
The Google-Only MSP That Turned Its Audit Into a SaaS
Jul 21, 2026
140 Clients, No Employees: How a Solo MSP Does It
Jul 11, 2026
Turn Clicks Into Cash: Conversion Hacks Every Business Needs
Dec 06, 2024
Don’t Dilute Your Ownership! The Debt vs Equity Debate Every Tech Founder Needs to Hear
Nov 29, 2024
The Path to Independent Success: Rand Fishkin on How to Build Without VC Funding
Oct 28, 2024
From Viral B2C AI Video templates to leading AI Video SaaS platform
Jul 31, 2024
How to be a Tech Disruptor in One of the Oldest Sports Industries of our Time
Jul 01, 2024
How to Build a Modern B2B Commerce Network
Jun 24, 2024
Leading WhatsApp Integrations SaaS for CRMs and Sales
Jun 18, 2024
Bootstrapping to $1m ARR while competing at American Ninja Warrior
Jun 11, 2024
How Grain Hit $1m ARR With Product Loops
Jun 03, 2024
How Culture Built a $30m ARR B2B SaaS
May 27, 2024
How Two Brothers Built a Waste Management SaaS
May 20, 2024
How DrugHunter Grew to $2M ARR
May 13, 2024
How This LinkedIn SaaS Hit $2M ARR With SEO
May 08, 2024
Bootstrapping eCom SaaS to $5m ARR
May 01, 2024
Rob Smith at Slick
Apr 16, 2024
Sam Shepler at Testimonial Hero
Apr 02, 2024
How to Build AI for Institutional Finance
Apr 02, 2024
How to Monetize Communities with Tech
Mar 20, 2024
Raised $16m to Build an AR & AI SaaS
Mar 11, 2024
Building a Martech SaaS
Mar 05, 2024
Will Your SaaS Get Acquired in 2024? TinySeed's Outlook
Feb 28, 2024
The Dangers of VC Funding in SaaS
Feb 20, 2024
How to Acquire Startups to Exit Your SaaS
Feb 12, 2024
SaaS Secrets from $40m Revenue Serial Founder
Feb 06, 2024
How to Bootstrap to $2.5m ARR Whilst Travelling The World
Jan 30, 2024
How to Sell Your SaaS Into Enterprise Compliantly
Jan 23, 2024
Exiting an Enterprise SaaS to a US Strategic Owned by Vista Equity
Jan 12, 2024