In this episode I sit down with Henry Kaskov, founder of Kaskov Valuations, for a raw, behind-the-scenes conversation about what it really takes to evaluate, grow, and eventually sell a business.
Henry has become the go-to guy when companies need to understand what their business is worth, when it’s the right time to sell, and how to position themselves for maximum valuation. Unlike theory-heavy startup podcasts, this conversation is about the messy middle: hiring the right people, delegating as a founder, making valuation adjustments, and preparing for big transitions like exits, divorce, or generational transfers.
You’ll learn:
✅ When to sell your business, and how to know if the timing is right
✅ How valuations really work (EBITDA, recurring revenue, multiples, and adjustments)
✅ Why hiring proactive, entrepreneurial employees is critical for scaling
✅How AI is disrupting valuations and marketing agencies (and how to stay ahead)The hidden truths about succession planning, divorce valuations, and generational business transfers
✅ Why building predictable revenue streams and reducing risk directly increases company value
This is the kind of real talk you won’t hear on highlight-reel shows like How I Built This or theory-driven shows like Masters of Scale. It’s no-fluff founder wisdom from someone who lives it every day.
If you’re an entrepreneur, aspiring founder, or business owner who wants to know the truth about valuations, exits, and building a business the smart way, this is your episode. Think of this as the best podcast for aspiring entrepreneurs who want authentic advice and behind-the-scenes founder stories.
Get in touch with Henry Kaskov:
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Timecodes
00:00 Introduction to Business Valuation
00:22 Challenges of Scaling a Business
02:04 Hiring the Right Team
04:26 Evaluating Business Worth
08:19 Preparing for Business Sale
12:09 Adjusting Financial Statements
18:15 Importance of Recurring Revenue
23:01 Timing the Sale of Your Business
27:26 Equity and Second Payouts
28:01 Building In-House Content Teams
28:21 Disruption in Marketing Agencies
29:35 AI's Impact on Business Valuation
37:39 The Role of Personal Goodwill in Divorce
45:12 Networking and Business Development
49:33 The Future of Business Transitions
54:20 Conclusion and Contact Information